Mechanism-Guided Design of Robust Palladium Catalysts for Selective Aerobic Oxidation of Polyols

Ramsay-Burrough, Summer; Marron, Daniel P.; Armstrong, Keith C.; Del Castillo, Trevor J.; Zare, Richard N.; Waymouth, Robert M.

doi:10.1021/jacs.2c10667

Mechanism-Guided Design of Robust Palladium Catalysts for Selective Aerobic Oxidation of Polyols

Journal Article · 19 January 2023 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.2c10667· OSTI ID:2420731

^[1]; ^[2]; ^[2]; ^[2]; ^[2]; ^[2]

Department of Chemistry, Stanford University, Stanford, California 94305, United States; OSTI
Department of Chemistry, Stanford University, Stanford, California 94305, United States

Not provided.

Research Organization:: Stanford Univ., CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0018168

OSTI ID:: 2420731

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 4 Vol. 145; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (51)

Catalytic Oxidations in a Bio-Based Economy Sheldon, Roger A. Frontiers in Chemistry, Vol. 8 https://doi.org/10.3389/fchem.2020.00132	journal	February 2020
Chemo- and Regioselective Oxidation of Secondary Alcohols in Vicinal Diols Eisink, Niek; Minnaard, Adriaan; Witte, Martin Synthesis, Vol. 49, Issue 04 https://doi.org/10.1055/s-0036-1589476	journal	January 2017
The application of electrospray ionization mass spectrometry to homogeneous catalysis Vikse, Krista L.; Ahmadi, Zohrab; Scott McIndoe, J. Coordination Chemistry Reviews, Vol. 279 https://doi.org/10.1016/j.ccr.2014.06.012	journal	November 2014
Fundamentals of green chemistry: efficiency in reaction design Sheldon, Roger A. Chem. Soc. Rev., Vol. 41, Issue 4 https://doi.org/10.1039/C1CS15219J	journal	January 2012
Transition metal based catalysts in the aerobic oxidation of alcohols Parmeggiani, Camilla; Cardona, Francesca Green Chemistry, Vol. 14, Issue 3 https://doi.org/10.1039/c2gc16344f	journal	January 2012
Selective Catalytic Oxidation of Unprotected Carbohydrates Chung, Kevin; Waymouth, Robert M. ACS Catalysis, Vol. 6, Issue 7 https://doi.org/10.1021/acscatal.6b01501	journal	June 2016
Highly Enantioselective Direct Synthesis of Endocyclic Vicinal Diamines through Chiral Ru(diamine)‐Catalyzed Hydrogenation of 2,2′‐Bisquinoline Derivatives Ma, Wenpeng; Zhang, Jianwei; Xu, Cong Angewandte Chemie, Vol. 128, Issue 41 https://doi.org/10.1002/ange.201608181	journal	September 2016
The influence of polarization functions on molecular orbital hydrogenation energies Hariharan, P. C.; Pople, J. A. Theoretica Chimica Acta, Vol. 28, Issue 3 https://doi.org/10.1007/BF00533485	journal	January 1973
Site-Selective Functionalization of Hydroxyl Groups in Carbohydrate Derivatives Dimakos, Victoria; Taylor, Mark S. Chemical Reviews, Vol. 118, Issue 23 https://doi.org/10.1021/acs.chemrev.8b00442	journal	December 2018
On the trail of dioxygen activation Hill, Craig L.; Weinstock, Ira A. Nature, Vol. 388, Issue 6640 https://doi.org/10.1038/40986	journal	July 1997
Selective Catalytic Oxidation of Glycerol to Dihydroxyacetone Painter, Ron M.; Pearson, David M.; Waymouth, Robert M. Angewandte Chemie International Edition, Vol. 49, Issue 49 https://doi.org/10.1002/anie.201004063	journal	October 2010
Controlled green oxidation Hill, Craig L. Nature, Vol. 401, Issue 6752 https://doi.org/10.1038/46704	journal	September 1999
Green, Catalytic Oxidation of Alcohols in Water Brink, G. t. Science, Vol. 287, Issue 5458 https://doi.org/10.1126/science.287.5458.1636	journal	March 2000
Organocatalytic Ring-Opening Polymerization of Morpholinones: New Strategies to Functionalized Polyesters Blake, Timothy R.; Waymouth, Robert M. Journal of the American Chemical Society, Vol. 136, Issue 26 https://doi.org/10.1021/ja503830c	journal	June 2014
Recent advancements and challenges of palladiumII-catalyzed oxidation reactions with molecular oxygen as the sole oxidant Gligorich, Keith M.; Sigman, Matthew S. Chemical Communications, Issue 26 https://doi.org/10.1039/b902868d	journal	January 2009
Green, Catalytic Oxidations of Alcohols Sheldon, Roger A.; Arends, Isabel W. C. E.; ten Brink, Gerd-Jan Accounts of Chemical Research, Vol. 35, Issue 9 https://doi.org/10.1021/ar010075n	journal	September 2002
N,O-ligated Pd(ii) complexes for catalytic alcohol oxidation Dornan, Laura M.; Clendenning, Gráinne M. A.; Pitak, Mateusz B. Catal. Sci. Technol., Vol. 4, Issue 8 https://doi.org/10.1039/C4CY00296B	journal	January 2014
From Biomass to the KarrikinsviaSelective Catalytic Oxidation of Hemicellulose‐Derived Butyl Xylosides and Glucosides Xiao, Ganyuan; Su, Gerard; Slawin, Alexandra M. Z. European Journal of Organic Chemistry, Vol. 2022, Issue 15 https://doi.org/10.1002/ejoc.202101308	journal	February 2022
Density‐functional thermochemistry. III. The role of exact exchange Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652 https://doi.org/10.1063/1.464913	journal	April 1993
Efficient and Selective Cu/Nitroxyl-Catalyzed Methods for Aerobic Oxidative Lactonization of Diols Xie, Xiaomin; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 137, Issue 11 https://doi.org/10.1021/jacs.5b01036	journal	March 2015
Stereoselective Protection-Free Modification of 3-Keto-saccharides Marinus, Nittert; Tahiri, Nabil; Duca, Margherita Organic Letters, Vol. 22, Issue 14 https://doi.org/10.1021/acs.orglett.0c01986	journal	July 2020
Palladium‐Catalyzed Oxidation of Glucose in Glycopeptides** Reintjens, Niels R. M.; Yakovlieva, Liubov; Marinus, Nittert European Journal of Organic Chemistry, Vol. 2022, Issue 25 https://doi.org/10.1002/ejoc.202200677	journal	July 2022
Electronic, steric, and temperature effects in the Pd(II)-biquinoline catalyzed aerobic oxidation of benzylic alcohols in water Buffin, Brian P.; Belitz, Nadine L.; Verbeke, Sara L. Journal of Molecular Catalysis A: Chemical, Vol. 284, Issue 1-2 https://doi.org/10.1016/j.molcata.2008.01.020	journal	April 2008
Ligand-controlled, transition-metal catalyzed site-selective modification of glycosides Shang, Weidong; He, Bin; Niu, Dawen Carbohydrate Research, Vol. 474 https://doi.org/10.1016/j.carres.2019.01.006	journal	February 2019
Oxidatively Resistant Ligands for Palladium-Catalyzed Aerobic Alcohol Oxidation Pearson, David M.; Conley, Nicholas R.; Waymouth, Robert M. Organometallics, Vol. 30, Issue 6 https://doi.org/10.1021/om101037k	journal	March 2011
Catalytic and Regioselective Oxidation of Carbohydrates To Synthesize Keto-Sugars under Mild Conditions Muramatsu, Wataru Organic Letters, Vol. 16, Issue 18 https://doi.org/10.1021/ol502344h	journal	September 2014
Regioselective Carbohydrate Oxidations: A Nuclear Magnetic Resonance (NMR) Study on Selectivity, Rate, and Side-Product Formation Eisink, Niek N. H. M.; Witte, Martin D.; Minnaard, Adriaan J. ACS Catalysis, Vol. 7, Issue 2 https://doi.org/10.1021/acscatal.6b03459	journal	January 2017
Catalytic Regioselective Oxidation of Glycosides Jäger, Manuel; Hartmann, Marcel; de Vries, Johannes G. Angewandte Chemie, Vol. 125, Issue 30 https://doi.org/10.1002/ange.201301662	journal	June 2013
Pd-Catalyzed Aerobic Oxidation Reactions: Strategies To Increase Catalyst Lifetimes Ho, Wilson C.; Chung, Kevin; Ingram, Andrew J. Journal of the American Chemical Society, Vol. 140, Issue 2 https://doi.org/10.1021/jacs.7b11372	journal	January 2018
Late‐Stage Modification of Aminoglycoside Antibiotics Overcomes Bacterial Resistance Mediated by APH(3’) Kinases Bastian, Andreas A.; Bastian, Maria; Jäger, Manuel Chemistry – A European Journal, Vol. 28, Issue 36 https://doi.org/10.1002/chem.202200883	journal	May 2022
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Lee, Chengteh; Yang, Weitao; Parr, Robert G. Physical Review B, Vol. 37, Issue 2 https://doi.org/10.1103/PhysRevB.37.785	journal	January 1988
Regioselective oxidation of unprotected 1,4 linked glucans Eisink, Niek N. H. M.; Lohse, Jonas; Witte, Martin D. Organic & Biomolecular Chemistry, Vol. 14, Issue 21 https://doi.org/10.1039/C6OB00608F	journal	January 2016
Chemoselective Pd-Catalyzed Oxidation of Polyols: Synthetic Scope and Mechanistic Studies Chung, Kevin; Banik, Steven M.; De Crisci, Antonio G. Journal of the American Chemical Society, Vol. 135, Issue 20 https://doi.org/10.1021/ja4008694	journal	May 2013
Deuteration enhances catalyst lifetime in palladium-catalysed alcohol oxidation Armenise, Nicola; Tahiri, Nabil; Eisink, Niek N. H. M. Chemical Communications, Vol. 52, Issue 10 https://doi.org/10.1039/C5CC08588H	journal	January 2016
Ligand-Promoted Palladium-Catalyzed Aerobic Oxidation Reactions Wang, Dian; Weinstein, Adam B.; White, Paul B. Chemical Reviews, Vol. 118, Issue 5 https://doi.org/10.1021/acs.chemrev.7b00334	journal	October 2017
Regioselective Manipulation of GlcNAc Provides Allosamine, Lividosamine, and Related Compounds Zhang, Ji; Eisink, Niek N. H. M.; Witte, Martin D. The Journal of Organic Chemistry, Vol. 84, Issue 2 https://doi.org/10.1021/acs.joc.8b01949	journal	December 2018
Can Donor Ligands Make Pd(OAc) ₂ a Stronger Oxidant? Access to Elusive Palladium(II) Reduction Potentials and Effects of Ancillary Ligands via Palladium(II)/Hydroquinone Redox Equilibria Bruns, David L.; Musaev, Djamaladdin G.; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 142, Issue 46 https://doi.org/10.1021/jacs.0c09464	journal	November 2020
Ruthenium/1,1′‐Bis(diphenylphosphino)ferrocene‐Catalysed Oppenauer Oxidation of Alcohols and Lactonisation of α,ω‐Diols using Methyl Isobutyl Ketone as Oxidant Nicklaus, Céline M.; Phua, Pim Huat; Buntara, Teddy Advanced Synthesis & Catalysis, Vol. 355, Issue 14-15 https://doi.org/10.1002/adsc.201300438	journal	September 2013
Trinuclear Pd ₃ O ₂ Intermediate in Aerobic Oxidation Catalysis Ingram, Andrew J.; Solis-Ibarra, Diego; Zare, Richard N. Angewandte Chemie International Edition, Vol. 53, Issue 22 https://doi.org/10.1002/anie.201400134	journal	April 2014
Highly Practical Copper(I)/TEMPO Catalyst System for Chemoselective Aerobic Oxidation of Primary Alcohols Hoover, Jessica M.; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 133, Issue 42 https://doi.org/10.1021/ja206230h	journal	October 2011
Site-Selective Dehydroxy-Chlorination of Secondary Alcohols in Unprotected Glycosides Zhang, Ji; Reintjens, Niels R. M.; Dhineshkumar, Jayaraman Organic Letters, Vol. 24, Issue 29 https://doi.org/10.1021/acs.orglett.2c01992	journal	July 2022
Protecting-group-free synthesis as an opportunity for invention Young, Ian S.; Baran, Phil S. Nature Chemistry, Vol. 1, Issue 3 https://doi.org/10.1038/nchem.216	journal	June 2009
On the Origin of Regioselectivity in Palladium‐Catalyzed Oxidation of Glucosides Wan, Ieng Chim (Steven); Hamlin, Trevor A.; Eisink, Niek N. H. M. European Journal of Organic Chemistry, Vol. 2021, Issue 4 https://doi.org/10.1002/ejoc.202001453	journal	January 2021
Self—Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian—Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules Hehre, W. J.; Ditchfield, R.; Pople, J. A. The Journal of Chemical Physics, Vol. 56, Issue 5, p. 2257-2261 https://doi.org/10.1063/1.1677527	journal	March 1972
Self‐Consistent Molecular‐Orbital Methods. IX. An Extended Gaussian‐Type Basis for Molecular‐Orbital Studies of Organic Molecules Ditchfield, R.; Hehre, W. J.; Pople, J. A. The Journal of Chemical Physics, Vol. 54, Issue 2 https://doi.org/10.1063/1.1674902	journal	January 1971
Mechanism of Catalytic Oxidation of Styrenes with Hydrogen Peroxide in the Presence of Cationic Palladium(II) Complexes Walker, Katherine L.; Dornan, Laura M.; Zare, Richard N. Journal of the American Chemical Society, Vol. 139, Issue 36 https://doi.org/10.1021/jacs.7b05413	journal	August 2017
Catalytic Role of Multinuclear Palladium–Oxygen Intermediates in Aerobic Oxidation Followed by Hydrogen Peroxide Disproportionation Ingram, Andrew J.; Walker, Katherine L.; Zare, Richard N. Journal of the American Chemical Society, Vol. 137, Issue 42 https://doi.org/10.1021/jacs.5b08719	journal	October 2015
Pd(II)-biquinoline catalyzed aerobic oxidation of alcohols in water Buffin, Brian P.; Clarkson, James P.; Belitz, Nadine L. Journal of Molecular Catalysis A: Chemical, Vol. 225, Issue 1 https://doi.org/10.1016/j.molcata.2004.08.035	journal	January 2005
Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals Hay, P. Jeffrey; Wadt, Willard R. The Journal of Chemical Physics, Vol. 82, Issue 1, p. 299-310 https://doi.org/10.1063/1.448975	journal	January 1985
Aerobic Alcohol Oxidation with Cationic Palladium Complexes: Insights into Catalyst Design and Decomposition Conley, Nicholas R.; Labios, Liezel A.; Pearson, David M. Organometallics, Vol. 26, Issue 23 https://doi.org/10.1021/om700492n	journal	November 2007
Site-selective oxidation, amination and epimerization reactions of complex polyols enabled by transfer hydrogenation Hill, Christopher K.; Hartwig, John F. Nature Chemistry, Vol. 9, Issue 12 https://doi.org/10.1038/nchem.2835	journal	August 2017

Similar Records

Pd-Catalyzed Aerobic Oxidation Reactions: Strategies To Increase Catalyst Lifetimes

Journal Article · 2018 · Journal of the American Chemical Society · OSTI ID:1539669

Pd-Catalyzed Aerobic Oxidation Reactions: Strategies To Increase Catalyst Lifetimes

Journal Article · 2017 · Journal of the American Chemical Society · OSTI ID:1594171

Structure-guided Design of Selective Inhibitors of Neuronal Nitric Oxide Synthase

Journal Article · 2014 · J. Med. Chem. 56: 3024-3032, 2013 · OSTI ID:1146436

Related Subjects

Chemistry

Mechanism-Guided Design of Robust Palladium Catalysts for Selective Aerobic Oxidation of Polyols

Citation Formats

References (51)

Similar Records

Related Subjects