Investigation of Nitrile Hydration Chemistry by Two Transition Metal Hydroxide Complexes: Mn–OH and Ni–OH Nitrile Insertion Chemistry

Anderson, Nickolas H.; Boncella, James M.; Tondreau, Aaron M.

doi:10.1021/acs.organomet.8b00687

Title: Investigation of Nitrile Hydration Chemistry by Two Transition Metal Hydroxide Complexes: Mn–OH and Ni–OH Nitrile Insertion Chemistry

Journal Article · 05 December 2018 · Organometallics

DOI: https://doi.org/10.1021/acs.organomet.8b00687 · OSTI ID:1487362

Anderson, Nickolas H. ^[1];

^[1];

^[1]

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

Herein we describe the synthesis of a series of nickel complexes, including the formation of [(^iPrPN^HP)Ni(PMe₃)][BPh₄] (^iPrPN^HP = HN(CH₂CH₂(PiPr₂))₂). The ability of this phosphine complex to perform the 1,2-addition of H₂O to produce the Ni–OH species [(^iPrPN^HP)NiOH][BPh₄] has been investigated. The nucleophilicity of the hydroxide moiety of both [(iPrPNHP)NiOH][BPh4] and the previously reported (^iPrPN^HP)MnOH(CO)₂ was investigated through the hydration of aryl and alkyl nitriles, leading to the formation of a number of metal carboxamide (RC(O)NH–) bonds. This reactivity generated complexes with the general structures of [(^iPrPN^HP)Ni(NHC(O)R)][BPh₄] for nickel and (^iPrPN^HP)Mn(NHC(O)R)(CO)₂ for manganese. Under catalytic conditions, the hydration of nitriles using nickel complexes yielded only a single turnover. However, (^iPrPN^HP)MnOH(CO)₂ produced several turnovers, and the reaction conditions were probed for optimization.

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Research Organization:: Los Alamos National Laboratory (LANL)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: 89233218CNA000001

OSTI ID:: 1487362

Report Number(s):: LA-UR-18-28930

Journal Information:: Organometallics, Journal Name: Organometallics Journal Issue: 24 Vol. 37; ISSN 0276-7333

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (50)

Catalytic Hydration of Benzonitrile and Acetonitrile using Nickel(0) Crestani, Marco G.; Arévalo, Alma; García, Juventino J. Advanced Synthesis & Catalysis, Vol. 348, Issue 6 https://doi.org/10.1002/adsc.200505382	journal	April 2006
Katalytische Hydrolyse von Acrylnitril zu Acrylamid unter milden Bedingungen Chin, Jik; Kim, J. H. Angewandte Chemie, Vol. 102, Issue 5 https://doi.org/10.1002/ange.19901020530	journal	May 1990
Spectroscopic Elucidation of a Peroxo Ni2(?-O2) Intermediate Derived from a Nickel(I) Complex and Dioxygen Kieber-Emmons, Matthew T.; Schenker, Ralph; Yap, Glenn P. A. Angewandte Chemie International Edition, Vol. 43, Issue 48 https://doi.org/10.1002/anie.200460747	journal	December 2004
Manganese-Catalyzed Hydrogen-Autotransfer C−C Bond Formation: α-Alkylation of Ketones with Primary Alcohols Peña-López, Miguel; Piehl, Patrick; Elangovan, Saravanakumar Angewandte Chemie International Edition, Vol. 55, Issue 48 https://doi.org/10.1002/anie.201607072	journal	October 2016
Hydrogenation of Esters to Alcohols Catalyzed by Defined Manganese Pincer Complexes Elangovan, Saravanakumar; Garbe, Marcel; Jiao, Haijun Angewandte Chemie International Edition, Vol. 55, Issue 49 https://doi.org/10.1002/anie.201607233	journal	September 2016
A Stable Manganese Pincer Catalyst for the Selective Dehydrogenation of Methanol Andérez-Fernández, María; Vogt, Lydia K.; Fischer, Steffen Angewandte Chemie International Edition, Vol. 56, Issue 2 https://doi.org/10.1002/anie.201610182	journal	December 2016
Manganese(I)-Catalyzed Enantioselective Hydrogenation of Ketones Using a Defined Chiral PNP Pincer Ligand Garbe, Marcel; Junge, Kathrin; Walker, Svenja Angewandte Chemie International Edition, Vol. 56, Issue 37 https://doi.org/10.1002/anie.201705471	journal	August 2017
Oxidative Transformations of Biosourced Alcohols Catalyzed by Earth-Abundant Transition Metals Nguyen, Duc Hanh; Morin, Yohann; Zhang, Lei ChemCatChem, Vol. 9, Issue 14 https://doi.org/10.1002/cctc.201700310	journal	June 2017
Unmasking the Action of Phosphinous Acid Ligands in Nitrile Hydration Reactions Catalyzed by Arene-Ruthenium(II) Complexes Tomás-Mendivil, Eder; Cadierno, Victorio; Menéndez, María I. Chemistry - A European Journal, Vol. 21, Issue 47 https://doi.org/10.1002/chem.201503076	journal	October 2015
Phosphinous Acid-Assisted Hydration of Nitriles: Understanding the Controversial Reactivity of Osmium and Ruthenium Catalysts González-Fernández, Rebeca; Crochet, Pascale; Cadierno, Victorio Chemistry - A European Journal, Vol. 23, Issue 60 https://doi.org/10.1002/chem.201703481	journal	October 2017
Molecularly Defined Manganese Pincer Complexes for Selective Transfer Hydrogenation of Ketones Perez, Marc; Elangovan, Saravanakumar; Spannenberg, Anke ChemSusChem, Vol. 10, Issue 1 https://doi.org/10.1002/cssc.201601057	journal	October 2016
Structural and functional models of nitrile hydratase Mascharak, Pradip K. Coordination Chemistry Reviews, Vol. 225, Issue 1-2 https://doi.org/10.1016/S0010-8545(01)00413-1	journal	February 2002
Frontiers in catalytic nitrile hydration: Nitrile and cyanohydrin hydration catalyzed by homogeneous organometallic complexes Ahmed, Takiya J.; Knapp, Spring Melody M.; Tyler, David R. Coordination Chemistry Reviews, Vol. 255, Issue 7-8 https://doi.org/10.1016/j.ccr.2010.08.018	journal	April 2011
Synthesis, characterization and application of nickel(II) complexes modified with N,N′,N″-pincer ligands Czerny, Frank; Döhlert, Peter; Weidauer, Maik Inorganica Chimica Acta, Vol. 425 https://doi.org/10.1016/j.ica.2014.10.003	journal	January 2015
Metal-catalyzed nitrile hydration reactions: The specific contribution of ruthenium García-Álvarez, Rocío; Francos, Javier; Tomás-Mendivil, Eder Journal of Organometallic Chemistry, Vol. 771 https://doi.org/10.1016/j.jorganchem.2013.11.042	journal	November 2014
The synthesis of PNP-supported low-spin nitro manganese(I) carbonyl complexes Tondreau, Aaron M.; Boncella, James M. Polyhedron, Vol. 116 https://doi.org/10.1016/j.poly.2016.04.007	journal	September 2016
Terminal NiII−OH/−OH2 complexes in trigonal bipyramidal geometries derived from H2O Lau, Nathanael; Sano, Yohei; Ziller, Joseph W. Polyhedron, Vol. 125 https://doi.org/10.1016/j.poly.2016.11.015	journal	March 2017
Asymmetric nitrile-hydration with bifunctional ruthenium catalysts bearing chiral N-sulfonyldiamine ligands Kamezaki, Shoko; Akiyama, Satoshi; Kayaki, Yoshihito Tetrahedron: Asymmetry, Vol. 21, Issue 9-10 https://doi.org/10.1016/j.tetasy.2010.03.011	journal	May 2010
Reaction Mechanism of Low-Spin Iron(III)- and Cobalt(III)-Containing Nitrile Hydratases: A Quantum Mechanics Investigation Prejanò, Mario; Marino, Tiziana; Rizzuto, Carmen Inorganic Chemistry, Vol. 56, Issue 21 https://doi.org/10.1021/acs.inorgchem.7b02121	journal	October 2017
1,2-Addition of Formic or Oxalic Acid to ^– N{CH ₂ CH ₂ (PiPr ₂ )} ₂ -Supported Mn(I) Dicarbonyl Complexes and the Manganese-Mediated Decomposition of Formic Acid Tondreau, Aaron M.; Boncella, James M. Organometallics, Vol. 35, Issue 12 https://doi.org/10.1021/acs.organomet.6b00274	journal	June 2016
Reversible 1,2-Addition of Water To Form a Nucleophilic Mn(I) Hydroxide Complex: A Thermodynamic and Reactivity Study Tondreau, Aaron M.; Michalczyk, Ryszard; Boncella, James M. Organometallics, Vol. 36, Issue 21 https://doi.org/10.1021/acs.organomet.7b00618	journal	September 2017
Manganese Pincer Complexes for the Base-Free, Acceptorless Dehydrogenative Coupling of Alcohols to Esters: Development, Scope, and Understanding Nguyen, Duc Hanh; Trivelli, Xavier; Capet, Frédéric ACS Catalysis, Vol. 7, Issue 3 https://doi.org/10.1021/acscatal.6b03554	journal	February 2017
Manganese-Catalyzed Sequential Hydrogenation of CO ₂ to Methanol via Formamide Kar, Sayan; Goeppert, Alain; Kothandaraman, Jotheeswari ACS Catalysis, Vol. 7, Issue 9 https://doi.org/10.1021/acscatal.7b02066	journal	August 2017
Catalytic Upgrading of Ethanol to n -Butanol via Manganese-Mediated Guerbet Reaction Kulkarni, Naveen V.; Brennessel, William W.; Jones, William D. ACS Catalysis, Vol. 8, Issue 2 https://doi.org/10.1021/acscatal.7b03653	journal	January 2018
Low-Valent Ruthenium and Iridium Hydride Complexes as Alternatives to Lewis Acid and Base Catalysts Murahashi, Shun-Ichi; Takaya, Hikaru Accounts of Chemical Research, Vol. 33, Issue 4 https://doi.org/10.1021/ar980085x	journal	February 2000
Catalytic C–S Cross-Coupling Reactions Employing Ni Complexes of Pyrrole-Based Pincer Ligands Venkanna, Gopaladasu T.; Arman, Hadi D.; Tonzetich, Zachary J. ACS Catalysis, Vol. 4, Issue 9 https://doi.org/10.1021/cs500874z	journal	August 2014
Fast Carbon Dioxide Fixation by 2,6-Pyridinedicarboxamidato-nickel(II)-hydroxide Complexes: Influence of Changes in Reactive Site Environment on Reaction Rates Huang, Deguang; Makhlynets, Olga V.; Tan, Lay Ling Inorganic Chemistry, Vol. 50, Issue 20 https://doi.org/10.1021/ic200942u	journal	October 2011
Synthesis of Binucleating Macrocycles and Their Nickel(II) Hydroxo- and Cyano-Bridged Complexes with Divalent Ions: Anatomical Variation of Ligand Features Zhang, Xiaofeng; Huang, Deguang; Chen, Yu-Sheng Inorganic Chemistry, Vol. 51, Issue 20 https://doi.org/10.1021/ic301506x	journal	October 2012
A Dinuclear Ni(I) System Having a Diradical Ni ₂ N ₂ Diamond Core Resting State: Synthetic, Structural, Spectroscopic Elucidation, and Reductive Bond Splitting Reactions Adhikari, Debashis; Mossin, Susanne; Basuli, Falguni Inorganic Chemistry, Vol. 47, Issue 22 https://doi.org/10.1021/ic801137p	journal	November 2008
New Derivatives of PCP-Type Pincer Complexes of Nickel Castonguay, Annie; Beauchamp, André L.; Zargarian, Davit Inorganic Chemistry, Vol. 48, Issue 7 https://doi.org/10.1021/ic801641u	journal	March 2009
Reactions of the Terminal Ni ^II −OH Group in Substitution and Electrophilic Reactions with Carbon Dioxide and Other Substrates: Structural Definition of Binding Modes in an Intramolecular Ni ^II ···Fe ^II Bridged Site Huang, Deguang; Holm, R. H. Journal of the American Chemical Society, Vol. 132, Issue 13 https://doi.org/10.1021/ja1003125	journal	April 2010
Activation of Water, Ammonia, and Other Small Molecules by PC _carbene P Nickel Pincer Complexes Gutsulyak, Dmitry V.; Piers, Warren E.; Borau-Garcia, Javier Journal of the American Chemical Society, Vol. 135, Issue 32 https://doi.org/10.1021/ja406742n	journal	July 2013
Selective Catalytic Hydrogenations of Nitriles, Ketones, and Aldehydes by Well-Defined Manganese Pincer Complexes Elangovan, Saravanakumar; Topf, Christoph; Fischer, Steffen Journal of the American Chemical Society, Vol. 138, Issue 28 https://doi.org/10.1021/jacs.6b03709	journal	July 2016
Manganese-Catalyzed Upgrading of Ethanol into 1-Butanol Fu, Shaomin; Shao, Zhihui; Wang, Yujie Journal of the American Chemical Society, Vol. 139, Issue 34 https://doi.org/10.1021/jacs.7b05939	journal	August 2017
Integrative CO ₂ Capture and Hydrogenation to Methanol with Reusable Catalyst and Amine: Toward a Carbon Neutral Methanol Economy Kar, Sayan; Sen, Raktim; Goeppert, Alain Journal of the American Chemical Society, Vol. 140, Issue 5 https://doi.org/10.1021/jacs.7b12183	journal	January 2018
CO Insertion Reactions into the M−OH Bonds of Monomeric Nickel and Palladium Hydroxides. Reversible Decarbonylation of a Hydroxycarbonyl Palladium Complex Cámpora, Juan; Palma, Pilar; del Río, Diego Organometallics, Vol. 23, Issue 8 https://doi.org/10.1021/om040002i	journal	April 2004
Fluoride Displacement by Lithium Reagents. An Improved Method for the Synthesis of Nickel Hydroxo, Alkoxo, and Amido Complexes Cámpora, Juan; Matas, Inmaculada; Palma, Pilar Organometallics, Vol. 24, Issue 12 https://doi.org/10.1021/om0489709	journal	May 2005
Synthesis and Reactivity of Nickel(II) Hydroxycarbonyl Species, NiCOOH-κ C Yoo, Changho; Kim, Jin; Lee, Yunho Organometallics, Vol. 32, Issue 23 https://doi.org/10.1021/om400881j	journal	November 2013
Rare [(NHC) ₂ Ni-OH]-Type Terminal Nickel Hydroxo and [(NHC) ₂ Ni]-Type Complexes of N / O -Functionalized N-Heterocyclic Carbenes as Precatalysts for Highly Desirable Base-Free Michael Reactions in Air at Ambient Temperature Samantaray, Manoja K.; Shaikh, Mobin M.; Ghosh, Prasenjit Organometallics, Vol. 28, Issue 7 https://doi.org/10.1021/om801186f	journal	March 2009
Efficient and selective N-alkylation of amines with alcohols catalysed by manganese pincer complexes Elangovan, Saravanakumar; Neumann, Jacob; Sortais, Jean-Baptiste Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms12641	journal	October 2016
Selective hydration of nitriles to amides catalysed by PCP pincer supported nickel( ii ) complexes Borau-Garcia, J.; Gutsulyak, D. V.; Burford, R. J. Dalton Transactions, Vol. 44, Issue 27 https://doi.org/10.1039/C4DT03902E	journal	January 2015
Well-defined phosphino-phenolate neutral nickel( ii ) catalysts for efficient (co)polymerization of norbornene and ethylene Zhang, Yan-Ping; Li, Wei-Wei; Li, Bai-Xiang Dalton Transactions, Vol. 44, Issue 16 https://doi.org/10.1039/C5DT00074B	journal	January 2015
Iron catalyzed CO ₂ hydrogenation to formate enhanced by Lewis acid co-catalysts Zhang, Yuanyuan; MacIntosh, Alex D.; Wong, Janice L. Chemical Science, Vol. 6, Issue 7 https://doi.org/10.1039/C5SC01467K	journal	January 2015
Aliphatic Mn–PNP complexes for the CO ₂ hydrogenation reaction: a base free mechanism Rawat, Kuber Singh; Pathak, Biswarup Catalysis Science & Technology, Vol. 7, Issue 15 https://doi.org/10.1039/C7CY00737J	journal	January 2017
Efficient and selective hydrogenation of amides to alcohols and amines using a well-defined manganese–PNN pincer complex Papa, Veronica; Cabrero-Antonino, Jose R.; Alberico, Elisabetta Chemical Science, Vol. 8, Issue 5 https://doi.org/10.1039/C7SC00138J	journal	January 2017
Regioselective deuteration of alcohols in D ₂ O catalysed by homogeneous manganese and iron pincer complexes Kar, Sayan; Goeppert, Alain; Sen, Raktim Green Chemistry, Vol. 20, Issue 12 https://doi.org/10.1039/C8GC01052H	journal	January 2018
A general and efficient Mn-catalyzed acceptorless dehydrogenative coupling of alcohols with hydroxides into carboxylates Shao, Zhihui; Wang, Yujie; Liu, Yaqian Organic Chemistry Frontiers, Vol. 5, Issue 8 https://doi.org/10.1039/C8QO00023A	journal	January 2018
A structure and reactivity analysis of monomeric Ni(ii)–hydroxo complexes prepared from water Powell-Jia, Darla; Ziller, Joseph W.; DiPasquale, Antonio G. Dalton Transactions, Issue 16 https://doi.org/10.1039/b820209e	journal	January 2009
Metal complexes of Co, Ni and Cu with the pincer ligand HN(CH₂CH₂PⁱPr₂)₂: preparation, characterization and electrochemistry Rozenel, Sergio S.; Kerr, John B.; Arnold, John Dalton Transactions, Vol. 40, Issue 40, p. 10397-10405 https://doi.org/10.1039/c1dt10599j	journal	January 2011
[2,6-Bis(diphenylphosphanyloxy)phenyl-κ ³ P , C ¹ , P ′]hydroxidonickel(II) Zargarian, Davit; Salah, Abderrahmen Acta Crystallographica Section E Structure Reports Online, Vol. 67, Issue 7 https://doi.org/10.1107/S1600536811014267	journal	June 2011

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Hydration of nitriles using a metal-ligand cooperative ruthenium pincer catalyst Guo, Beibei; De Vries, Johannes G.; Otten, Edwin Cambridge : RSC https://doi.org/10.34657/5759	other	January 2019

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