Engineering Catalysts for Selective Ester Hydrogenation

Dub, Pavel A.; Batrice, Rami John; Gordon, John Cameron; Scott, Brian Lindley; Minko, Yury; Schmidt, Jurgen G.; Williams, Robert F.

doi:10.1021/acs.oprd.9b00559

Title: Engineering Catalysts for Selective Ester Hydrogenation

Journal Article · Thu Jan 30 00:00:00 UTC 2020 · Organic Process Research & Development

DOI: https://doi.org/10.1021/acs.oprd.9b00559 · OSTI ID:1605131

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Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

The development of efficient catalysts and processes for synthesizing functionalized (olefinic and/or chiral) primary alcohols and fluoral hemiacetals is currently needed. These are valuable building blocks for pharmaceuticals, agrochemicals, perfumes, and so forth. From an economic standpoint, bench-stable Takasago Int. Corp.’s Ru-PNP, more commonly known as Ru-MACHO, and Gusev’s Ru-SNS complexes are arguably the most appealing molecular catalysts to access primary alcohols from esters and H₂. This work introduces economically competitive Ru-SNP(O)_z complexes (z = 0, 1), which combine key structural elements of both of these catalysts. In particular, the incorporation of SNP heteroatoms into the ligand skeleton was found to be crucial for the design of a more product-selective catalyst in the synthesis of fluoral hemiacetals under kinetically controlled conditions. Based on experimental observations and computational analysis, this paper further extends the current state-of-the-art understanding of the accelerative role of KO-t-C₄H₉ in ester hydrogenation. Finally, it attempts to explain why a maximum turnover is seen to occur starting at ~25 mol % base, in contrast to only ~10 mol % with ketones as substrates.

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Research Organization:: Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)

Sponsoring Organization:: USDOE Laboratory Directed Research and Development (LDRD) Program; USDOE National Nuclear Security Administration (NNSA)

Grant/Contract Number:: 89233218CNA000001

OSTI ID:: 1605131

Report Number(s):: LA-UR--19-31371

Journal Information:: Organic Process Research & Development, Journal Name: Organic Process Research & Development Journal Issue: 3 Vol. 24; ISSN 1083-6160

Publisher:: ACS PublicationsCopyright Statement

Country of Publication:: United States

Language:: English

References (105)

Noyori's Hydrogenation Catalyst Needs a Lewis Acid Cocatalyst for High Activity We thank Mr. Christian Dambouwy, Thales Technologies AG, Zürich, Switzerland, for experimental work to compare the effects of various combinations of bases and salts. Additionally, we thank Mr. Holgar Sellner in the group of Prof. D. Seebach for assistance in ee measurements, and Sebastian D. Friess for carefully correcting the German version of this manuscript. Hartmann, Rudolf; Chen, Peter Angewandte Chemie International Edition, Vol. 40, Issue 19 https://doi.org/10.1002/1521-3773(20011001)40:19<3581::aid-anie3581>3.0.co;2-7	journal	October 2001
Catalytic Hydrogenation of Chiral α-Amino and α-Hydroxy Esters at Room Temperature with Nishimura Catalyst without Racemization Studer, Martin; Burkhardt, Stefan; Blaser, Hans-Ulrich Advanced Synthesis & Catalysis, Vol. 343, Issue 8 https://doi.org/10.1002/1615-4169(20011231)343:8<802::aid-adsc802>3.0.co;2-t	journal	December 2001
Inexpensive Ruthenium NNS-Complexes as Efficient Ester Hydrogenation Catalysts with High C=O vs. C=C Selectivities Stadler, Bernhard M.; Puylaert, Pim; Diekamp, Justus Advanced Synthesis & Catalysis, Vol. 360, Issue 6 https://doi.org/10.1002/adsc.201701607	journal	January 2018
Structure and Reactivity of Lithium Enolates. From Pinacolone to SelectiveC-Alkylations of Peptides. Difficulties and Opportunities Afforded by Complex Structures Seebach, Dieter Angewandte Chemie International Edition in English, Vol. 27, Issue 12 https://doi.org/10.1002/anie.198816241	journal	December 1988
Dihydrogen Reduction of Carboxylic Esters to Alcohols under the Catalysis of Homogeneous Ruthenium Complexes: High Efficiency and Unprecedented Chemoselectivity Saudan, Lionel A.; Saudan, Christophe M.; Debieux, Catherine Angewandte Chemie International Edition, Vol. 46, Issue 39 https://doi.org/10.1002/anie.200701015	journal	October 2007
The NH Functional Group in Organometallic Catalysis Zhao, Baoguo; Han, Zhaobin; Ding, Kuiling Angewandte Chemie International Edition, Vol. 52, Issue 18 https://doi.org/10.1002/anie.201204921	journal	March 2013
Replacing Phosphorus with Sulfur for the Efficient Hydrogenation of Esters Spasyuk, Denis; Smith, Samantha; Gusev, Dmitry G. Angewandte Chemie International Edition, Vol. 52, Issue 9 https://doi.org/10.1002/anie.201209218	journal	January 2013
Non-Pincer-Type Manganese Complexes as Efficient Catalysts for the Hydrogenation of Esters van Putten, Robbert; Uslamin, Evgeny A.; Garbe, Marcel Angewandte Chemie International Edition, Vol. 56, Issue 26 https://doi.org/10.1002/anie.201701365	journal	April 2017
Base‐Free Iron Catalyzed Transfer Hydrogenation of Esters Using EtOH as Hydrogen Source Farrar‐Tobar, Ronald A.; Wozniak, Bartosz; Savini, Arianna Angewandte Chemie International Edition, Vol. 58, Issue 4 https://doi.org/10.1002/anie.201810605	journal	January 2019
New Ruthenium Complexes Based on Tetradentate Bipyridine Ligands for Catalytic Hydrogenation of Esters Wang, Fangyuan; Tan, Xuefeng; Lv, Hui Chemistry - An Asian Journal, Vol. 11, Issue 15 https://doi.org/10.1002/asia.201600506	journal	July 2016
Unexpected Direct Hydride Transfer Mechanism for the Hydrogenation of Ethyl Acetate to Ethanol Catalyzed by SNS Pincer Ruthenium Complexes Chen, Xiangyang; Jing, Yuanyuan; Yang, Xinzheng Chemistry - A European Journal, Vol. 22, Issue 6 https://doi.org/10.1002/chem.201504058	journal	January 2016
Isomerization of Allylic Alcohols to Ketones Catalyzed by Well-Defined Iron PNP Pincer Catalysts Xia, Tian; Wei, Zhihong; Spiegelberg, Brian Chemistry - A European Journal, Vol. 24, Issue 16 https://doi.org/10.1002/chem.201705454	journal	January 2018
Enantioselective Friedel-Crafts reaction of indoles with trifluoroacetaldehyde catalyzed by Cinchona alkaloids Borkin, Dmitry A.; Landge, Shainaz M.; Török, Béla Chirality, Vol. 23, Issue 8 https://doi.org/10.1002/chir.20982	journal	July 2011
Scope and Mechanism on Iridium-f-Amphamide Catalyzed Asymmetric Hydrogenation of Ketones Liang, Zhiqin; Yang, Tilong; Gu, Guoxian Chinese Journal of Chemistry, Vol. 36, Issue 9 https://doi.org/10.1002/cjoc.201800129	journal	July 2018
UCSF Chimera?A visualization system for exploratory research and analysis Pettersen, Eric F.; Goddard, Thomas D.; Huang, Conrad C. Journal of Computational Chemistry, Vol. 25, Issue 13 https://doi.org/10.1002/jcc.20084	journal	January 2004
Semiempirical GGA-type density functional constructed with a long-range dispersion correction Grimme, Stefan Journal of Computational Chemistry, Vol. 27, Issue 15, p. 1787-1799 https://doi.org/10.1002/jcc.20495	journal	January 2006
Biotechnological production of enantiomerically pure d-lactic acid Klotz, Silvia; Kaufmann, Norman; Kuenz, Anja Applied Microbiology and Biotechnology, Vol. 100, Issue 22 https://doi.org/10.1007/s00253-016-7843-7	journal	September 2016
Effect of solvent polarity on the regioselective hydroxyalkylation of indole with trifluoroacetaldehyde hemiacetals Peerannawar, Swarada; Sood, Abha; Brown, Alicia Structural Chemistry, Vol. 30, Issue 5 https://doi.org/10.1007/s11224-019-01386-x	journal	July 2019
Liquid phase isomerization of isoprenol into prenol in hydrogen environment Kogan, S.; Kaliya, M.; Froumin, N. Applied Catalysis A: General, Vol. 297, Issue 2 https://doi.org/10.1016/j.apcata.2005.09.010	journal	January 2006
Challenges and opportunities in lactic acid bioprocess design—From economic to production aspects Alves de Oliveira, Regiane; Komesu, Andrea; Vaz Rossell, Carlos Eduardo Biochemical Engineering Journal, Vol. 133 https://doi.org/10.1016/j.bej.2018.03.003	journal	May 2018
Top value platform chemicals: bio-based production of organic acids Becker, Judith; Lange, Anna; Fabarius, Jonathan Current Opinion in Biotechnology, Vol. 36 https://doi.org/10.1016/j.copbio.2015.08.022	journal	December 2015
Copper(I) complexes of N-centered aliphatic tripodal trithioether ligands – Adjustment of complex geometry by variation of spacer lengths Blomenkemper, Marc; Schröder, Henning; Pape, Tania Inorganica Chimica Acta, Vol. 366, Issue 1 https://doi.org/10.1016/j.ica.2010.10.008	journal	January 2011
Computational insights into the catalytic role of the base promoters in ester hydrogenation with homogeneous non-pincer-based Mn-P,N catalyst Liu, Chong; van Putten, Robbert; Kulyaev, Pavel O. Journal of Catalysis, Vol. 363 https://doi.org/10.1016/j.jcat.2018.04.018	journal	July 2018
The species- and site-specific acid–base properties of biological thiols and their homodisulfides Mirzahosseini, Arash; Noszál, Béla Journal of Pharmaceutical and Biomedical Analysis, Vol. 95 https://doi.org/10.1016/j.jpba.2014.02.023	journal	July 2014
Ruthenium complexes bearing amino-bis(phosphinite) or amino-bis(aminophosphine) ligands: Application in catalytic ester hydrogenation Henrion, Mickaël; Roisnel, Thierry; Couturier, Jean-Luc Molecular Catalysis, Vol. 432 https://doi.org/10.1016/j.mcat.2017.01.025	journal	May 2017
Redox-responsive flower-like micelles of poly(l-lactic acid)-b-poly(ethylene glycol)-b-poly(l-lactic acid) for intracellular drug delivery Yang, Qinglai; He, Changyu; Zhang, Zhen Polymer, Vol. 90 https://doi.org/10.1016/j.polymer.2016.03.030	journal	May 2016
Synthesis of the molecular hybrid inspired by Largazole and Psammaplin A Yu, Xiaoling; Zhang, Bingbing; Shan, Guangsheng Tetrahedron, Vol. 74, Issue 5 https://doi.org/10.1016/j.tet.2017.12.025	journal	February 2018
Microwave-assisted preparation of trifluoroacetaldehyde (fluoral): isolation and applications Landge, Shainaz M.; Borkin, Dmitry A.; Török, Béla Tetrahedron Letters, Vol. 48, Issue 36 https://doi.org/10.1016/j.tetlet.2007.06.170	journal	September 2007
Recent application of oxa-Michael reaction in complex natural product synthesis Hu, Jialei; Bian, Ming; Ding, Hanfeng Tetrahedron Letters, Vol. 57, Issue 50 https://doi.org/10.1016/j.tetlet.2016.11.007	journal	December 2016
Biorefineries for the production of top building block chemicals and their derivatives Choi, Sol; Song, Chan Woo; Shin, Jae Ho Metabolic Engineering, Vol. 28 https://doi.org/10.1016/j.ymben.2014.12.007	journal	March 2015
Production of muconic acid in plants Eudes, Aymerick; Berthomieu, Roland; Hao, Zhangying Metabolic Engineering, Vol. 46 https://doi.org/10.1016/j.ymben.2018.02.002	journal	March 2018
Synthesis and corrected structures of sulphur-containing amides from Glycosmis species: Sinharines, penimides, and illukumbins Hinterberger, Sabine; Hofer, Otmar; Greger, Harald Tetrahedron, Vol. 50, Issue 21 https://doi.org/10.1016/s0040-4020(01)80647-5	journal	January 1994
Hemiaminals of trifluoroacetaldehyde, as trifluoromethylating agents Mispelaere, Clotilde; Roques, Nicolas Tetrahedron Letters, Vol. 40, Issue 35 https://doi.org/10.1016/s0040-4039(99)01369-6	journal	August 1999
Homogeneous Catalysis for Sustainable Hydrogen Storage in Formic Acid and Alcohols Sordakis, Katerina; Tang, Conghui; Vogt, Lydia K. Chemical Reviews, Vol. 118, Issue 2 https://doi.org/10.1021/acs.chemrev.7b00182	journal	October 2017
Polymer–Temozolomide Conjugates as Therapeutics for Treating Glioblastoma Ward, Sarah M.; Skinner, Matthew; Saha, Banishree Molecular Pharmaceutics, Vol. 15, Issue 11 https://doi.org/10.1021/acs.molpharmaceut.8b00766	journal	October 2018
SNS-Ligands for Ru-Catalyzed Homogeneous Hydrogenation and Dehydrogenation Reactions Schörgenhumer, Johannes; Zimmermann, Axel; Waser, Mario Organic Process Research & Development, Vol. 22, Issue 7 https://doi.org/10.1021/acs.oprd.8b00142	journal	June 2018
Air-Stable NNS (ENENES) Ligands and Their Well-Defined Ruthenium and Iridium Complexes for Molecular Catalysis Dub, Pavel A.; Scott, Brian L.; Gordon, John C. Organometallics, Vol. 34, Issue 18 https://doi.org/10.1021/acs.organomet.5b00432	journal	June 2015
Atmospheric Hydrogenation of Esters Catalyzed by PNP-Ruthenium Complexes with an N -Heterocyclic Carbene Ligand Ogata, Osamu; Nakayama, Yuji; Nara, Hideki Organic Letters, Vol. 18, Issue 15 https://doi.org/10.1021/acs.orglett.6b01900	journal	July 2016
Enantioselective Iridium-Catalyzed Hydrogenation of α-Keto Amides to α-Hydroxy Amides Gu, Guoxian; Yang, Tilong; Yu, Ouran Organic Letters, Vol. 19, Issue 21 https://doi.org/10.1021/acs.orglett.7b02912	journal	October 2017
N -Monomethylation of Aromatic Amines with Methanol via PN ^H P-Pincer Ru Catalysts Ogata, Osamu; Nara, Hideki; Fujiwhara, Mitsuhiko Organic Letters, Vol. 20, Issue 13 https://doi.org/10.1021/acs.orglett.8b01449	journal	June 2018
ESI-MS Insights into Acceptorless Dehydrogenative Coupling of Alcohols Vicent, Cristian; Gusev, Dmitry G. ACS Catalysis, Vol. 6, Issue 5 https://doi.org/10.1021/acscatal.6b00623	journal	April 2016
Dehydrogenative Coupling of Ethanol and Ester Hydrogenation Catalyzed by Pincer-Type YNP Complexes Gusev, Dmitry G. ACS Catalysis, Vol. 6, Issue 10 https://doi.org/10.1021/acscatal.6b02324	journal	September 2016
Metal–Ligand Bifunctional Catalysis: The “Accepted” Mechanism, the Issue of Concertedness, and the Function of the Ligand in Catalytic Cycles Involving Hydrogen Atoms Dub, Pavel A.; Gordon, John C. ACS Catalysis, Vol. 7, Issue 10 https://doi.org/10.1021/acscatal.7b01791	journal	September 2017
Deeper Mechanistic Insight into Ru Pincer-Mediated Acceptorless Dehydrogenative Coupling of Alcohols: Exchanges, Intermediates, and Deactivation Species Nguyen, Duc Hanh; Trivelli, Xavier; Capet, Frédéric ACS Catalysis, Vol. 8, Issue 5 https://doi.org/10.1021/acscatal.8b00995	journal	April 2018
The path of chemical reactions - the IRC approach Fukui, Kenichi Accounts of Chemical Research, Vol. 14, Issue 12 https://doi.org/10.1021/ar00072a001	journal	December 1981
Catalytic Reductive Transformations of Carboxylic and Carbonic Acid Derivatives Using Molecular Hydrogen Dub, Pavel A.; Ikariya, Takao ACS Catalysis, Vol. 2, Issue 8 https://doi.org/10.1021/cs300341g	journal	July 2012
Computational Mechanistic Study of Fe-Catalyzed Hydrogenation of Esters to Alcohols: Improving Catalysis by Accelerating Precatalyst Activation with a Lewis Base Qu, Shuanglin; Dai, Huiguang; Dang, Yanfeng ACS Catalysis, Vol. 4, Issue 12 https://doi.org/10.1021/cs501089h	journal	November 2014
Performance of Density Functional Theory for Second Row (4 d ) Transition Metal Thermochemistry Laury, Marie L.; Wilson, Angela K. Journal of Chemical Theory and Computation, Vol. 9, Issue 9 https://doi.org/10.1021/ct400379z	journal	August 2013
X-ray crystal structures of lithium, sodium, and potassium enolates of pinacolone Williard, Paul G.; Carpenter, Gene B. Journal of the American Chemical Society, Vol. 108, Issue 3 https://doi.org/10.1021/ja00263a016	journal	February 1986
X-ray crystal structure of an unsolvated lithium enolate anion Williard, Paul G.; Carpenter, Gene B. Journal of the American Chemical Society, Vol. 107, Issue 11 https://doi.org/10.1021/ja00297a049	journal	May 1985
Structures of three lithium ester enolates by x-ray diffraction: derivation of reaction path for cleavage into ketene and alcoholate Seebach, Dieter; Amstutz, Rene; Laube, Thomas Journal of the American Chemical Society, Vol. 107, Issue 19 https://doi.org/10.1021/ja00305a014	journal	September 1985
Mechanism of Asymmetric Hydrogenation of Ketones Catalyzed by BINAP/1,2-Diamine−Ruthenium(II) Complexes Sandoval, Christian A.; Ohkuma, Takeshi; Muñiz, Kilian Journal of the American Chemical Society, Vol. 125, Issue 44 https://doi.org/10.1021/ja030272c	journal	November 2003
An Unexpected Possible Role of Base in Asymmetric Catalytic Hydrogenations of Ketones. Synthesis and Characterization of Several Key Catalytic Intermediates Hamilton, Robin J.; Bergens, Steven H. Journal of the American Chemical Society, Vol. 128, Issue 42 https://doi.org/10.1021/ja065460s	journal	October 2006
Catalytic Hydrogenation of Carboxamides and Esters by Well-Defined Cp*Ru Complexes Bearing a Protic Amine Ligand Ito, Masato; Ootsuka, Takashi; Watari, Ryo Journal of the American Chemical Society, Vol. 133, Issue 12 https://doi.org/10.1021/ja1117254	journal	March 2011
Oxo-Tethered Ruthenium(II) Complex as a Bifunctional Catalyst for Asymmetric Transfer Hydrogenation and H ₂ Hydrogenation Touge, Taichiro; Hakamata, Tomohiko; Nara, Hideki Journal of the American Chemical Society, Vol. 133, Issue 38 https://doi.org/10.1021/ja207283t	journal	September 2011
Base-Catalyzed Bifunctional Addition to Amides and Imides at Low Temperature. A New Pathway for Carbonyl Hydrogenation John, Jeremy M.; Takebayashi, Satoshi; Dabral, Nupur Journal of the American Chemical Society, Vol. 135, Issue 23 https://doi.org/10.1021/ja401294q	journal	May 2013
Practical Selective Hydrogenation of α-Fluorinated Esters with Bifunctional Pincer-Type Ruthenium(II) Catalysts Leading to Fluorinated Alcohols or Fluoral Hemiacetals Otsuka, Takashi; Ishii, Akihiro; Dub, Pavel A. Journal of the American Chemical Society, Vol. 135, Issue 26 https://doi.org/10.1021/ja403852e	journal	June 2013
Unravelling the Mechanism of the Asymmetric Hydrogenation of Acetophenone by [RuX ₂ (diphosphine)(1,2-diamine)] Catalysts Dub, Pavel A.; Henson, Neil J.; Martin, Richard L. Journal of the American Chemical Society, Vol. 136, Issue 9 https://doi.org/10.1021/ja411374j	journal	February 2014
Tuning of the Copper–Thioether Bond in Tetradentate N ₃ S _(thioether) Ligands; O–O Bond Reductive Cleavage via a [Cu ^II ₂ (μ-1,2-peroxo)] ²⁺ /[Cu ^III ₂ (μ-oxo) ₂ ] ²⁺ Equilibrium Kim, Sunghee; Ginsbach, Jake W.; Billah, A. Imtiaz Journal of the American Chemical Society, Vol. 136, Issue 22 https://doi.org/10.1021/ja502974c	journal	May 2014
Chemoselective Hydrogenation of Carbonyl Compounds and Acceptorless Dehydrogenative Coupling of Alcohols Spasyuk, Denis; Vicent, Cristian; Gusev, Dmitry G. Journal of the American Chemical Society, Vol. 137, Issue 11 https://doi.org/10.1021/ja512389y	journal	March 2015
Bis-N-heterocyclic Carbene Aminopincer Ligands Enable High Activity in Ru-Catalyzed Ester Hydrogenation Filonenko, Georgy A.; Aguila, Mae Joanne B.; Schulpen, Erik N. Journal of the American Chemical Society, Vol. 137, Issue 24 https://doi.org/10.1021/jacs.5b04237	journal	June 2015
Why Does Alkylation of the N–H Functionality within M/NH Bifunctional Noyori-Type Catalysts Lead to Turnover? Dub, Pavel A.; Scott, Brian L.; Gordon, John C. Journal of the American Chemical Society, Vol. 139, Issue 3 https://doi.org/10.1021/jacs.6b11666	journal	January 2017
Electron Transfer Reactions: KO t Bu (but not NaO t Bu) Photoreduces Benzophenone under Activation by Visible Light Nocera, Giuseppe; Young, Allan; Palumbo, Fabrizio Journal of the American Chemical Society, Vol. 140, Issue 30 https://doi.org/10.1021/jacs.8b06089	journal	July 2018
Dehydroalkylative Activation of CNN- and PNN-Pincer Ruthenium Catalysts for Ester Hydrogenation He, Tianyi; Buttner, John C.; Reynolds, Eamon F. Journal of the American Chemical Society, Vol. 141, Issue 43 https://doi.org/10.1021/jacs.9b09326	journal	October 2019
The self-condensation reaction of lithium ester enolates. Isolation of a ketene intermediate Sullivan, Donald F.; Woodbury, Richard P.; Rathke, Michael W. The Journal of Organic Chemistry, Vol. 42, Issue 11 https://doi.org/10.1021/jo00431a058	journal	May 1977
Molecular Structure and Internal Rotation of CF ₃ Group of Methyl Trifluoroacetate: Gas Electron Diffraction, Microwave Spectroscopy, and Quantum Chemical Calculation Studies Kuze, Nobuhiko; Ishikawa, Atsushi; Kono, Maho The Journal of Physical Chemistry A, Vol. 119, Issue 9 https://doi.org/10.1021/jp508447b	journal	September 2014
Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions Marenich, Aleksandr V.; Cramer, Christopher J.; Truhlar, Donald G. The Journal of Physical Chemistry B, Vol. 113, Issue 18, p. 6378-6396 https://doi.org/10.1021/jp810292n	journal	May 2009
N -Heterocyclic Carbene Catalyzed Highly Chemoselective Intermolecular Crossed Acyloin Condensation of Aromatic Aldehydes with Trifluoroacetaldehyde Ethyl Hemiacetal Ramanjaneyulu, Bandaru T.; Mahesh, Sriram; Vijaya Anand, Ramasamy Organic Letters, Vol. 17, Issue 1 https://doi.org/10.1021/ol502581b	journal	December 2014
Highly Efficient Tetradentate Ruthenium Catalyst for Ester Reduction: Especially for Hydrogenation of Fatty Acid Esters Tan, Xuefeng; Wang, Yan; Liu, Yuanhua Organic Letters, Vol. 17, Issue 3 https://doi.org/10.1021/ol503456j	journal	January 2015
Hydrogenation of Esters Catalyzed by Ruthenium PN ³ -Pincer Complexes Containing an Aminophosphine Arm Chen, Tao; Li, Huaifeng; Qu, Shuanglin Organometallics, Vol. 33, Issue 15 https://doi.org/10.1021/om500549t	journal	July 2014
Catalytic Hydrogenation of Esters. Development of an Efficient Catalyst and Processes for Synthesising ( R )-1,2-Propanediol and 2-( l -Menthoxy)ethanol Kuriyama, Wataru; Matsumoto, Takaji; Ogata, Osamu Organic Process Research & Development, Vol. 16, Issue 1 https://doi.org/10.1021/op200234j	journal	November 2011
Catalytic Hydrogenation of Carboxylic Acid Esters, Amides, and Nitriles with Homogeneous Catalysts Werkmeister, Svenja; Junge, Kathrin; Beller, Matthias Organic Process Research & Development, Vol. 18, Issue 2 https://doi.org/10.1021/op4003278	journal	January 2014
The role of the metal-bound N–H functionality in Noyori-type molecular catalysts Dub, Pavel A.; Gordon, John C. Nature Reviews Chemistry, Vol. 2, Issue 12 https://doi.org/10.1038/s41570-018-0049-z	journal	November 2018
High-effective approach from amino acid esters to chiral amino alcohols over Cu/ZnO/Al2O3 catalyst and its catalytic reaction mechanism Zhang, Shuangshuang; Yu, Jun; Li, Huiying Scientific Reports, Vol. 6, Issue 1 https://doi.org/10.1038/srep33196	journal	September 2016
The first tridentate phosphine ligand combining planar, phosphorus and carbon chiralityElectronic supplementary information (ESI) available: experimental section. See http://www.rsc.org/suppdata/cc/b2/b208384a/ Barbaro, Pierluigi; Bianchini, Claudio; Giambastiani, Giuliano Chemical Communications, Issue 22 https://doi.org/10.1039/b208384a	journal	October 2002
Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy Weigend, Florian; Ahlrichs, Reinhart Physical Chemistry Chemical Physics, Vol. 7, Issue 18, p. 3297-3305 https://doi.org/10.1039/b508541a	journal	January 2005
Accurate Coulomb-fitting basis sets for H to Rn Weigend, Florian Physical Chemistry Chemical Physics, Vol. 8, Issue 9 https://doi.org/10.1039/b515623h	journal	January 2006
The oxa-Michael reaction: from recent developments to applications in natural product synthesis Nising, Carl F.; Bräse, Stefan Chemical Society Reviews, Vol. 37, Issue 6 https://doi.org/10.1039/b718357g	journal	January 2008
Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections Chai, Jeng-Da; Head-Gordon, Martin Physical Chemistry Chemical Physics, Vol. 10, Issue 44 https://doi.org/10.1039/b810189b	journal	January 2008
Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s “Top 10” revisited Bozell, Joseph J.; Petersen, Gene R. Green Chemistry, Vol. 12, Issue 4, p. 539-554 https://doi.org/10.1039/b922014c	journal	January 2010
Recent developments in the field of oxa-Michael reactions Nising, Carl F.; Bräse, Stefan Chem. Soc. Rev., Vol. 41, Issue 3 https://doi.org/10.1039/c1cs15167c	journal	January 2012
A biocatalytic hydrogenation of carboxylic acids Ni, Yan; Hagedoorn, Peter-Leon; Xu, Jian-He Chemical Communications, Vol. 48, Issue 99 https://doi.org/10.1039/c2cc36479d	journal	January 2012
Ruthenium complexes of tetradentate bipyridine ligands: highly efficient catalysts for the hydrogenation of carboxylic esters and lactones Li, Wei; Xie, Jian-Hua; Yuan, Ming-Lei Green Chemistry, Vol. 16, Issue 9 https://doi.org/10.1039/c4gc00835a	journal	January 2014
The synthesis and application of a diazirine-modified uridine analogue for investigating RNA–protein interactions Smith, Christine C.; Hollenstein, Marcel; Leumann, Christian J. RSC Adv., Vol. 4, Issue 89 https://doi.org/10.1039/c4ra08682a	journal	January 2014
A new designed hydrazine group-containing ruthenium complex used for catalytic hydrogenation of esters Tan, Xuefeng; Wang, Qingli; Liu, Yuanhua Chemical Communications, Vol. 51, Issue 61 https://doi.org/10.1039/c5cc04242a	journal	January 2015
Heterogeneous and homogeneous catalysis for the hydrogenation of carboxylic acid derivatives: history, advances and future directions Pritchard, James; Filonenko, Georgy A.; van Putten, Robbert Chemical Society Reviews, Vol. 44, Issue 11 https://doi.org/10.1039/c5cs00038f	journal	January 2015
Production of acrylic acid from biomass-derived allyl alcohol by selective oxidation using Au/ceria catalysts Yang, Sungpil; Kim, Minsu; Yang, Sungeun Catalysis Science & Technology, Vol. 6, Issue 10 https://doi.org/10.1039/c5cy02099a	journal	January 2016
Chiral Brønsted acid-catalyzed enantioselective Friedel–Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated in situ Kondoh, Azusa; Ota, Yusuke; Komuro, Takazumi Chemical Science, Vol. 7, Issue 2 https://doi.org/10.1039/c5sc03175c	journal	January 2016
Cooperative interplay between a flexible PNN-Ru( ii ) complex and a NaBH ₄ additive in the efficient catalytic hydrogenation of esters Wang, Zheng; Chen, Xiangyang; Liu, Bo Catalysis Science & Technology, Vol. 7, Issue 6 https://doi.org/10.1039/c6cy02413k	journal	January 2017
The mechanism of enantioselective ketone reduction with Noyori and Noyori–Ikariya bifunctional catalysts Dub, Pavel A.; Gordon, John C. Dalton Transactions, Vol. 45, Issue 16 https://doi.org/10.1039/c6dt00476h	journal	January 2016
Glycerol as a potential renewable raw material for acrylic acid production Sun, Daolai; Yamada, Yasuhiro; Sato, Satoshi Green Chemistry, Vol. 19, Issue 14 https://doi.org/10.1039/c7gc00358g	journal	January 2017
Catalytic hydrogenation of carboxylic acids using low-valent and high-valent metal complexes Yoshioka, Shota; Saito, Susumu Chemical Communications, Vol. 54, Issue 95 https://doi.org/10.1039/c8cc06543h	journal	January 2018
Sustainable organophosphorus-catalysed Staudinger reduction Lenstra, Danny C.; Lenting, Peter E.; Mecinović, Jasmin Green Chemistry, Vol. 20, Issue 19 https://doi.org/10.1039/c8gc02136h	journal	January 2018
Methylenomycin B: A New Synthesis from a β-Ketophosphonate Mikołajczyk, Marian; Bałczewski, Piotr Synthesis, Vol. 1987, Issue 07 https://doi.org/10.1055/s-1987-28041	journal	January 1987
Inhomogeneous Electron Gas Hohenberg, P.; Kohn, W. Physical Review, Vol. 136, Issue 3B, p. B864-B871 https://doi.org/10.1103/physrev.136.b864	journal	November 1964
Self-Consistent Equations Including Exchange and Correlation Effects Kohn, W.; Sham, L. J. Physical Review, Vol. 140, Issue 4A, p. A1133-A1138 https://doi.org/10.1103/physrev.140.a1133	journal	November 1965
The Path Forward for Biofuels and Biomaterials Ragauskas, Arthur J.; Williams, Charlotte K.; Davison, Brian H. Science, Vol. 311, Issue 5760, p. 484-489 https://doi.org/10.1126/science.1114736	journal	January 2006
A Simple Method for the Esterification of Carboxylic Acids Using Chlorosilanes Nakao, Ren; Oka, Kunio; Fukumoto, Tsugio Bulletin of the Chemical Society of Japan, Vol. 54, Issue 4 https://doi.org/10.1246/bcsj.54.1267	journal	April 1981
Cofactor Recycling for Selective Enzymatic Biotransformation of Cinnamaldehyde to Cinnamyl Alcohol Zucca, Paolo; Littarru, Maria; Rescigno, Antonio Bioscience, Biotechnology, and Biochemistry, Vol. 73, Issue 5 https://doi.org/10.1271/bbb.90025	journal	May 2009
Top Value Added Chemicals From Biomass: I. Results of Screening for Potential Candidates from Sugars and Synthesis Gas Werpy, Todd A.; Holladay, John E.; White, James F. https://doi.org/10.2172/926125	report	November 2004
L-Lysine Fermentation Anastassiadis, Savas Recent Patents on Biotechnology, Vol. 1, Issue 1 https://doi.org/10.2174/187220807779813947	journal	February 2007
Biotechnological Production of Fumaric Acid: The Effect of Morphology of Rhizopus arrhizus NRRL 2582 Papadaki, Aikaterini; Androutsopoulos, Nikolaos; Patsalou, Maria Fermentation, Vol. 3, Issue 3 https://doi.org/10.3390/fermentation3030033	journal	July 2017
Fumaric Acid Production: A Biorefinery Perspective Martin-Dominguez, Victor; Estevez, Juliana; Ojembarrena, Francisco Fermentation, Vol. 4, Issue 2 https://doi.org/10.3390/fermentation4020033	journal	May 2018
A Convenient Synthesis of Amino Acid Methyl Esters Li, Jiabo; Sha, Yaowu Molecules, Vol. 13, Issue 5 https://doi.org/10.3390/molecules13051111	journal	May 2008
Synthesis and properties of alkylthioethanals Keiko, Natalia A.; Stepanova, Ludmila G.; Verochkina, Ekaterina A. Arkivoc, Vol. 2011, Issue 10 https://doi.org/10.3998/ark.5550190.0012.a11	journal	August 2011

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
base effect
ester hydrogenation
fluoral hemiacetal
homogeneous catalysis
mechanism

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