Amine synthesis via transition metal homogeneous catalysed hydrosilylation

Amines are among the most important compounds due to their wide applications in several areas of importance. Among the numerous synthetic methodologies, this review provides a comprehensive summary of the preparation of amines involving homogeneous transition metal catalysed hydrosilylation methodologies including the reduction of imine, amide, nitro and nitrile derivatives. In addition, challenging tandem reactions such as reductive amination or the use of CO2 as a C1-building block in N-methylation of amines will also be discussed.

[1]  Richard C. Larock,et al.  Comprehensive organic transformations : a guide to functional group preparations , 2018 .

[2]  Woo‐Jin Yoo,et al.  Chelating Bis(1,2,3-triazol-5-ylidene) Rhodium Complexes: Versatile Catalysts for Hydrosilylation Reactions , 2016 .

[3]  J. Młynarski,et al.  Diastereoselective Hydrosilylation of N‐(tert‐Butylsulfinyl)imines Catalyzed by Zinc Acetate , 2016 .

[4]  Joseph A. R. Schmidt,et al.  Selective hydrosilylation of N-allylimines using a (3-iminophosphine)palladium precatalyst , 2016 .

[5]  Stephen P. Thomas,et al.  Chemoselective nitro reduction and hydroamination using a single iron catalyst† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c5sc04471e , 2016, Chemical science.

[6]  J. Młynarski,et al.  Enantioselective Hydrosilylation of Imines Catalyzed by Chiral Zinc Acetate Complexes. , 2016, The Journal of organic chemistry.

[7]  B. Jiang,et al.  Copper N-Heterocyclic Carbene: A Catalyst for Aerobic Oxidation or Reduction Reactions. , 2015, Organic letters.

[8]  D. Michalik,et al.  Selective rhodium-catalyzed reduction of tertiary amides in amino acid esters and peptides. , 2015, Angewandte Chemie.

[9]  Xi‐Cun Wang,et al.  Selective reduction of nitro-compounds to primary amines by nickel-catalyzed hydrosilylative reduction , 2015 .

[10]  Yukihiro Motoyama,et al.  Catalyst Design of Vaska-Type Iridium Complexes for Highly Efficient Synthesis of π-Conjugated Enamines , 2015 .

[11]  Thomas E. La Cruz,et al.  Practical olefin hydroamination with nitroarenes , 2015, Science.

[12]  M. Beller,et al.  A Mild and Selective Reduction of β‐Lactams: Rh‐Catalyzed Hydrosilylation towards Important Pharmacological Building Blocks , 2015 .

[13]  J. Djukic,et al.  Efficient hydrosilylation of imines using catalysts based on iridium(III) metallacycles , 2015 .

[14]  Juventino J. García,et al.  Selective N-Methylation of Aliphatic Amines with CO2 and Hydrosilanes Using Nickel-Phosphine Catalysts , 2015 .

[15]  A. Volkov,et al.  Mild and selective Et2Zn-catalyzed reduction of tertiary amides under hydrosilylation conditions. , 2015, Organic letters.

[16]  A. Volkov,et al.  Mo(CO)6 catalysed chemoselective hydrosilylation of α,β-unsaturated amides for the formation of allylamines. , 2014, Chemical communications.

[17]  Jean‐Baptiste Sortais,et al.  Methylation of secondary amines with dialkyl carbonates and hydrosilanes catalysed by iron complexes. , 2014, Chemical communications.

[18]  M. Beller,et al.  Direct catalytic N-alkylation of amines with carboxylic acids. , 2014, Journal of the American Chemical Society.

[19]  H. Klare,et al.  Direct catalytic access to N-silylated enamines from enolizable imines and hydrosilanes by base-free dehydrogenative Si-N coupling. , 2014, Chemistry.

[20]  G. Sekar,et al.  Chemoselective reduction of α-keto amides using nickel catalysts. , 2014, Chemical communications.

[21]  C. Bruneau,et al.  Iron-catalysed tandem isomerisation/hydrosilylation reaction of allylic alcohols with amines , 2014 .

[22]  Olivier Jacquet,et al.  Iron-catalyzed hydrosilylation of CO2: CO2 conversion to formamides and methylamines , 2014 .

[23]  M. Beller,et al.  Mild Hydrosilylation of Amides by Platinum N‐Heterocyclic Carbene Catalysts , 2014 .

[24]  P. Dixneuf,et al.  Sequential Ruthenium(II)-Acetate Catalyzed C–H Bond Diarylation in NMP or Water and Hydrosilylation of Imines , 2014, Topics in Catalysis.

[25]  Thomas Dombray,et al.  Cobalt Carbonyl-Based Catalyst for Hydrosilylation of Carboxamides , 2013 .

[26]  J. Epping,et al.  Bis-N-heterocyclic carbene (NHC) stabilized η6-arene iron(0) complexes: synthesis, structure, reactivity, and catalytic activity. , 2013, Journal of the American Chemical Society.

[27]  Mickaël Henrion,et al.  Cyclopentadienyl N-heterocyclic carbene–nickel complexes as efficient pre-catalysts for the hydrosilylation of imines , 2013 .

[28]  Pedro R. Florindo,et al.  Efficient and chemoselective direct reductive amination of aromatic aldehydes catalyzed by oxo–rhenium complexes containing heterocyclic ligands , 2013 .

[29]  T. Hollis,et al.  Homobimetallic Rhodium NHC Complexes as Versatile Catalysts for Hydrosilylation of a Multitude of Substrates in the Presence of Ambient Air , 2013 .

[30]  M. Driess,et al.  N-Heterocyclic Silylene (NHSi) Rhodium and Iridium Complexes: Synthesis, Structure, Reactivity, and Catalytic Ability , 2013 .

[31]  B. Zohour,et al.  Cover Picture: New Insights into the Oxidative Coupling of Methane from Spatially Resolved Concentration and Temperature Profiles (ChemCatChem 10/2013) , 2013 .

[32]  G. Nikonov,et al.  Unexpected Role of Zinc Hydride in Catalytic Hydrosilylation of Ketones and Nitriles , 2013 .

[33]  C. D. F. Königs,et al.  Catalytic 1,4-selective hydrosilylation of pyridines and benzannulated congeners. , 2013, Angewandte Chemie.

[34]  M. Beller,et al.  A general catalytic methylation of amines using carbon dioxide. , 2013, Angewandte Chemie.

[35]  D. Gutsulyak,et al.  Chemo- and Regioselective Catalytic Reduction of N-Heterocycles by Silane , 2013 .

[36]  P. Ghorai,et al.  Stereoselective direct reductive amination of ketones with electron-deficient amines using Re2O7/NaPF6 catalyst. , 2013, Organic & biomolecular chemistry.

[37]  Jean‐Baptiste Sortais,et al.  Unexpected selectivity in ruthenium-catalyzed hydrosilylation of primary amides: synthesis of secondary amines. , 2013, Chemical communications.

[38]  O. Jacquet,et al.  CO2 as a C1-building block for the catalytic methylation of amines , 2013 .

[39]  A. Volkov,et al.  Direct Hydrosilylation of Tertiary Amides to Amines by an In Situ Formed Iron/N-Heterocyclic Carbene Catalyst , 2013 .

[40]  G. Du,et al.  Scope and Mechanistic Studies of Catalytic Hydrosilylation with a High-Valent Nitridoruthenium(VI) , 2013 .

[41]  B. Breit,et al.  Catalytic hydrogenation of amides to amines under mild conditions. , 2013, Angewandte Chemie.

[42]  C. Senanayake,et al.  A Practical Procedure for Reduction of Primary, Secondary and Tertiary Amides to Amines , 2013 .

[43]  S. Enthaler,et al.  Reductive cleavage of amides to alcohols and amines catalyzed by well-defined bimetallic molybdenum complexes. , 2012, Chemistry.

[44]  Mickaël Henrion,et al.  Hydrosilylation of Aldehydes and Ketones Catalyzed by an N‐Heterocyclic Carbene‐Nickel Hydride Complex under Mild Conditions , 2012 .

[45]  B. Royo,et al.  N-Heterocyclic Carbene Complexes of Nickel as Efficient Catalysts for Hydrosilylation of Carbonyl Derivatives , 2012 .

[46]  J. Khinast,et al.  Tethered ansa-bridged titanium complexes immobilized on 3-mercaptopropyl-functionalized silica gel and their application for the hydrosilylation of imines. , 2012, Dalton transactions.

[47]  J. Djukic,et al.  Room temperature tandem hydroamination and hydrosilation/protodesilation catalysis by a tricarbonylchromium-bound iridacycle. , 2012, Chemical communications.

[48]  V. Dorcet,et al.  Phosphane‐Pyridine Iron Complexes: Synthesis, Characterization and Application in Reductive Amination through the Hydrosilylation Reaction , 2012 .

[49]  M. Brookhart,et al.  Iridium-catalyzed reduction of secondary amides to secondary amines and imines by diethylsilane. , 2012, Journal of the American Chemical Society.

[50]  T. Nishikata,et al.  N alkylation of tosylamides using esters as primary and tertiary alkyl sources: mediated by hydrosilanes activated by a ruthenium catalyst. , 2012, Angewandte Chemie.

[51]  F. E. Kühn,et al.  Rhodium-Catalyzed Hydrosilylation of Ketones: Catalyst Development and Mechanistic Insights , 2012 .

[52]  M. Beller,et al.  A general and selective copper-catalyzed reduction of secondary amides. , 2012, Chemical communications.

[53]  M. Beller,et al.  Two iron catalysts are better than one: a general and convenient reduction of aromatic and aliphatic primary amides. , 2012, Angewandte Chemie.

[54]  B. Li,et al.  Amine synthesis through mild catalytic hydrosilylation of imines using polymethylhydroxysiloxane and [RuCl2(arene)]2 catalysts. , 2012, ChemSusChem.

[55]  M. Brookhart,et al.  Development and mechanistic investigation of a highly efficient iridium(V) silyl complex for the reduction of tertiary amides to amines. , 2012, Journal of the American Chemical Society.

[56]  L. C. M. Castro,et al.  NHC-carbene cyclopentadienyl iron based catalyst for a general and efficient hydrosilylation of imines. , 2012, Chemical communications.

[57]  G. Venkanna,et al.  Well‐Defined Cyclopentadienyl NHC Iron Complex as the Catalyst for Efficient Hydrosilylation of Amides to Amines and Nitriles , 2011 .

[58]  A. C. Fernandes,et al.  A novel efficient and chemoselective method for the reduction of nitriles using the system silane/oxo-rhenium complexes , 2011 .

[59]  M. Beller,et al.  Zinc-catalyzed chemoselective reduction of tertiary and secondary amides to amines. , 2011, Chemistry.

[60]  W. Brennessel,et al.  Synthesis and reactivity of new Ni, Pd, and Pt 2,6-bis(di-tert-butylphosphinito)pyridine pincer complexes. , 2011, Inorganic chemistry.

[61]  B. Li,et al.  Sequential Catalysis for the Production of Sterically Hindered Amines: Ru(II)-Catalyzed C–H Bond Activation and Hydrosilylation of Imines , 2011 .

[62]  Xinhui Feng,et al.  Enantioselective Hydrosilylation of Imines Catalyzed by Diamine-Zinc Complexes , 2011 .

[63]  A. Favre-Réguillon,et al.  Hydrosiloxane–Ti(OiPr)4: an efficient system for the reduction of primary amides into primary amines as their hydrochloride salts , 2011 .

[64]  M. Beller,et al.  Selective reduction of carboxylic acid derivatives by catalytic hydrosilylation. , 2011, Angewandte Chemie.

[65]  H. Nagashima,et al.  New catalyst systems for iron-catalyzed hydrosilane reduction of carboxamides. , 2011, Chemical communications.

[66]  Jadwiga Gajewy,et al.  Convenient, enantioselective hydrosilylation of imines in protic media catalyzed by a Zn-trianglamine complex. , 2011, Organic & biomolecular chemistry.

[67]  Shou‐Fei Zhu,et al.  Transition metal-catalyzed enantioselective hydrogenation of enamines and imines. , 2011, Chemical reviews.

[68]  D. Gutsulyak,et al.  Facile catalytic hydrosilylation of pyridines. , 2011, Angewandte Chemie.

[69]  S. Enthaler,et al.  Synthesis of Secondary Amines by Iron‐Catalyzed Reductive Amination , 2010 .

[70]  C. Claver,et al.  Highlights of Transition Metal‐Catalyzed Asymmetric Hydrogenation of Imines , 2010 .

[71]  D. Gutsulyak,et al.  Chemoselective catalytic hydrosilylation of nitriles. , 2010, Angewandte Chemie.

[72]  A. C. Fernandes,et al.  Efficient and Highly Chemoselective Direct Reductive Amination of Aldehydes using the System Silane/Oxorhenium Complexes , 2010 .

[73]  Yusuke Kobayashi,et al.  Enantioselective reduction of ketones and imines catalyzed by (CN-box)Re(V)-oxo complexes. , 2010, Chemistry.

[74]  Marc Lemaire,et al.  Iron-catalyzed selective reduction of nitro compounds to amines , 2010 .

[75]  A. Papworth,et al.  Selective Hydrogenation of Amides using Ruthenium/ Molybdenum Catalysts , 2010 .

[76]  M. Beller,et al.  Iron-catalyzed selective reduction of nitroarenes to anilines using organosilanes. , 2010, Chemical communications.

[77]  P. Kalck,et al.  Mechanistic analysis of the transition metal-catalyzed hydrogenation of imines and functionalized enamines , 2010 .

[78]  M. Beller,et al.  Zinc-catalyzed reduction of amides: unprecedented selectivity and functional group tolerance. , 2010, Journal of the American Chemical Society.

[79]  M. Beller,et al.  A convenient and general iron-catalyzed reduction of amides to amines. , 2009, Angewandte Chemie.

[80]  Yukihiro Motoyama,et al.  Hydrosilane reduction of tertiary carboxamides by iron carbonyl catalysts. , 2009, Angewandte Chemie.

[81]  Yukihiro Motoyama,et al.  Practical access to amines by platinum-catalyzed reduction of carboxamides with hydrosilanes: synergy of dual Si-H groups leads to high efficiency and selectivity. , 2009, Journal of the American Chemical Society.

[82]  Rita G de Noronha,et al.  Highly chemo- and regioselective reduction of aromatic nitro compounds using the system silane/oxo-rhenium complexes. , 2009, The Journal of organic chemistry.

[83]  M. Beller,et al.  New catalytic properties of iron complexes: dehydration of amides to nitriles. , 2009, Chemical communications.

[84]  J. L. Fry,et al.  Ionic and Organometallic-Catalyzed Organosilane Reductions , 2009 .

[85]  J. Khinast,et al.  Titanocene-Catalyzed Hydrosilylation of Imines: Experimental and Computational Investigations of the Catalytically Active Species , 2009 .

[86]  M. Pink,et al.  Catalytic Hydrosilylation of the Carbonyl Functionality via a Transient Nickel Hydride Complex , 2009 .

[87]  Yukihiro Motoyama,et al.  Highly efficient synthesis of aldenamines from carboxamides by iridium-catalyzed silane-reduction/dehydration under mild conditions. , 2009, Chemical communications.

[88]  S. Chakraborty,et al.  Hydrosilylation of Aldehydes and Ketones Catalyzed by Nickel PCP-Pincer Hydride Complexes , 2009 .

[89]  A. Spannenberg,et al.  Menthyl-Substituted Group 4 Metallocene Dihalides , 2008 .

[90]  S. B. Halligudi,et al.  A chiral Mn(III) salen complex immobilized onto ionic liquid modified mesoporous silica for oxidative kinetic resolution of secondary alcohols , 2008 .

[91]  C. Deutsch,et al.  CuH-catalyzed reactions. , 2008, Chemical reviews.

[92]  Scott J. Miller,et al.  Selective partial reduction of quinolines: Hydrosilylation vs. transfer hydrogenation , 2008 .

[93]  O. Riant Hydrosilylation of Imines , 2008 .

[94]  P. Andersson,et al.  Modern Reduction Methods , 2008 .

[95]  S. Nolan,et al.  Copper, silver, and gold complexes in hydrosilylation reactions. , 2008, Accounts of chemical research.

[96]  E. Alberico,et al.  Chapter 1.3. Transferhydrogenations , 2008 .

[97]  S. Nolan,et al.  TRANSITION METAL-CATALYZED HYDROSILYLATION OF CARBONYL COMPOUNDS AND IMINES. A REVIEW , 2007 .

[98]  Yukihiro Motoyama,et al.  Functional group-selective poisoning of molecular catalysts: a ruthenium cluster-catalysed highly amide-selective silane reduction that does not affect ketones or esters. , 2007, Chemical communications.

[99]  Yukihiro Motoyama,et al.  The ruthenium-catalyzed reduction and reductive N-alkylation of secondary amides with hydrosilanes: practical synthesis of secondary and tertiary amines by judicious choice of hydrosilanes. , 2007, The Journal of organic chemistry.

[100]  D. Cole-Hamilton,et al.  The synthesis of amines by the homogeneous hydrogenation of secondary and primary amides. , 2007, Chemical communications.

[101]  C. Romão,et al.  Reduction of amides with silanes catalyzed by MoO2Cl2 , 2007 .

[102]  H. Nishiyama,et al.  An iron-catalysed hydrosilylation of ketones. , 2007, Chemical communications.

[103]  M. Oestreich,et al.  Polishing a diamond in the rough: "Cu--H" catalysis with silanes. , 2007, Angewandte Chemie.

[104]  S. Peng,et al.  Intra- and Intermolecular Hydroamination of Alkynes Catalyzed by ortho-Metalated Iridium Complexes , 2007 .

[105]  Yukihiro Motoyama,et al.  Dual Si–H effects in platinum-catalyzed silane reduction of carboxamides leading to a practical synthetic process of tertiary-amines involving self-encapsulation of the catalyst species into the insoluble silicone resin formed , 2006 .

[106]  J. Yun,et al.  Zinc‐Catalyzed Enantioselective Hydrosilylation of Imines , 2006 .

[107]  B. Marciniec Catalysis by transition metal complexes of alkene silylation – recent progress and mechanistic implications , 2005 .

[108]  Yukihiro Motoyama,et al.  Catalytic Reduction of Amides to Amines with Hydrosilanes Using a Triruthenium Carbonyl Cluster as the Catalyst , 2005 .

[109]  R. Maleczka,et al.  Pd-catalyzed silicon hydride reductions of aromatic and aliphatic nitro groups. , 2005, Organic letters.

[110]  Yukihiro Motoyama,et al.  Self-encapsulation of homogeneous catalyst species into polymer gel leading to a facile and efficient separation system of amine products in the Ru-catalyzed reduction of carboxamides with polymethylhydrosiloxane (PMHS). , 2005, Journal of the American Chemical Society.

[111]  Richard W. Ahn,et al.  Enantioselective reduction of imines catalyzed by a rhenium(V)-oxo complex. , 2005, Journal of the American Chemical Society.

[112]  L. Field,et al.  Iridium(I)‐Catalysed Tandem Hydrosilylation‐Protodesilylation of Imines , 2005 .

[113]  T. Iwasawa,et al.  A Bowl-Shaped Phosphine as a Ligand in Rhodium-Catalyzed Hydrosilylation: Rate Enhancement by a Mono(phosphine) Rhodium Species , 2005 .

[114]  Frauke Pohlki,et al.  Hydroamination/hydrosilylation sequence catalyzed by titanium complexes. , 2005, Angewandte Chemie.

[115]  S. Sakaguchi,et al.  Catalytic reductive alkylation of secondary amine with aldehyde and silane by an iridium compound. , 2005, The Journal of organic chemistry.

[116]  R. Morris,et al.  Mechanisms of the H2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexes , 2004 .

[117]  O. Riant,et al.  Recent advances in the asymmetric hydrosilylation of ketones, imines and electrophilic double bonds , 2004 .

[118]  Kerstin M. Mueller,et al.  Amines: Synthesis, Properties and Applications , 2004 .

[119]  K. Selvakumar,et al.  The titanocene-catalyzed reduction of acetamides to tertiary amines by PhMeSiH2 , 2004 .

[120]  F. Ferioli,et al.  New chiral 1,2-diamines and their use in zinc.catalyzed asymmetric hydrosilylation of acetophenone , 2004 .

[121]  B. Lipshutz,et al.  Copper(I)-catalyzed asymmetric hydrosilylations of imines at ambient temperatures. , 2004, Angewandte Chemie.

[122]  A. Mortreux,et al.  New developments in zinc-catalyzed asymmetric hydrosilylation of ketones with PMHS , 2004 .

[123]  D. Zargarian,et al.  Hydrosilylation of alkenes and ketones catalyzed by nickel(II) indenyl complexes , 2003 .

[124]  L. Field,et al.  One-Pot Tandem Hydroamination/Hydrosilation Catalyzed by Cationic Iridium(I) Complexes , 2003 .

[125]  M. Kira,et al.  Stoichiometric Hydrosilylation of Nitriles and Catalytic Hydrosilylation of Imines and Ketones Using a μ-Silane Diruthenium Complex , 2003 .

[126]  F. Toste,et al.  Reversing the Role of the Metal−Oxygen π-Bond. Chemoselective Catalytic Reductions with a Rhenium(V)-Dioxo Complex , 2003 .

[127]  A. Mortreux,et al.  Direct Zn-diamine promoted reduction of C=O and C=N bonds by polymethylhydrosiloxane in methanol. , 2003, Chemical communications.

[128]  Jean-François Carpentier and Virginie Bette Chemo- and Enantioselective Hydrosilylation of Carbonyl and Imino Groups. An Emphasis on Non-Traditional Catalyst Systems , 2002 .

[129]  H. Nagashima,et al.  A triruthenium carbonyl cluster bearing a bridging acenaphthylene ligand: an efficient catalyst for reduction of esters, carboxylic acids, and amides by trialkylsilanes. , 2002, The Journal of organic chemistry.

[130]  Y. Nishibayashi,et al.  Ruthenium-catalysed asymmetric hydrosilylation of ketoximes using chiral oxazolinylferrocenylphosphines. , 2001, Chemical communications.

[131]  Mamoru Igarashi,et al.  Transition-metal complex-catalyzed reduction of amides with hydrosilanes: a facile transformation of amides to amines , 2001 .

[132]  A. Ricci Modern Amination Methods , 2000 .

[133]  S. Buchwald,et al.  A method for the asymmetric hydrosilylation of N-aryl imines. , 2000, Organic letters.

[134]  S. Buchwald,et al.  Efficient kinetic resolution in the asymmetric hydrosilylation of imines of 3-substituted indanones and 4-substituted tetralones. , 2000, The Journal of organic chemistry.

[135]  G. Martra,et al.  Hydrosilylation of aromatic nitriles promoted by solvated rhodium atom-derived catalysts , 1999 .

[136]  J. Laumer,et al.  Enantioselective Reduction of Ketones by Polymethylhydrosiloxane in the Presence of Chiral Zinc Catalysts , 1999 .

[137]  K. Takehira,et al.  Dehydrogenative Silylation of Amines and Hydrosilylation of Imines Catalyzed by Ytterbium−Imine Complexes , 1999 .

[138]  Y. Nishibayashi,et al.  Iridium-Catalyzed Asymmetric Hydrosilylation of Imines Using Chiral Oxazolinyl-Phosphine Ligands , 1999 .

[139]  S. Buchwald,et al.  Synthesis of NPS R-568 utilizing titanium-catalyzed asymmetric hydrosilylation , 1999 .

[140]  Y. Mu,et al.  Homogeneous Catalytic Hydrosilylation of Pyridines. , 1998, Angewandte Chemie.

[141]  S. Buchwald,et al.  Short Enantioselective Total Syntheses of the Piperidine Alkaloids (S)-Coniine and (2R,6R)-trans-Solenopsin A via Catalytic Asymmetric Imine Hydrosilylation. , 1998, The Journal of organic chemistry.

[142]  C. Bolm,et al.  Transition Metals for Organic Synthesis , 1998 .

[143]  Y. Nishibayashi,et al.  RUTHENIUM-CATALYZED ASYMMETRIC HYDROSILYLATION OF KETONES AND IMINE , 1998 .

[144]  S. Buchwald,et al.  Amine Additives Greatly Expand the Scope of Asymmetric Hydrosilylation of Imines. , 1998, Angewandte Chemie.

[145]  R. Kuwano,et al.  REDUCTION OF AMIDES TO AMINES VIA CATALYTIC HYDROSILYLATION BY A RHODIUM COMPLEX , 1998 .

[146]  R. Noyori,et al.  Asymmetric Activation of Racemic Ruthenium(II) Complexes for Enantioselective Hydrogenation , 1998 .

[147]  A. Tillack,et al.  The hydrosilylation of ald-and ketimines catalyzed by titanocene complexes , 1997 .

[148]  and Ryoji Noyori,et al.  Asymmetric Transfer Hydrogenation Catalyzed by Chiral Ruthenium Complexes , 1997 .

[149]  S. Buchwald,et al.  Highly Enantioselective Imine Hydrosilylation Using (S,S)-Ethylenebis(η5-tetrahydroindenyl)titanium Difluoride , 1996 .

[150]  S. Buchwald,et al.  A Mild General Procedure for the One‐Pot Conversion of Amides to Aldehydes , 1996 .

[151]  W. Miles,et al.  The Reduction of Nitrobenzenes by Triethylsilane Using Wilkinson's Catalyst , 1996 .

[152]  W. M. Davis,et al.  Preparation of Novel Titanium Complexes Bearing o-Phosphinophenol Ligands , 1996 .

[153]  S. Buchwald,et al.  An Inexpensive Air-Stable Titanium-Based System for the Conversion of Esters to Primary Alcohols , 1995 .

[154]  A. Berkessel,et al.  Nickel Complex Catalyzed Reduction of Imines , 1995 .

[155]  T. Ikariya,et al.  PRACTICAL ENANTIOSELECTIVE HYDROGENATION OF AROMATIC KETONES , 1995 .

[156]  S. Buchwald,et al.  Enantioselective hydrosilylation of ketones with a chiral titanocene catalyst , 1994 .

[157]  S. Buchwald,et al.  Titanocene-Catalyzed Reduction of Esters Using Polymethylhydrosiloxane as the Stoichiometric Reductant , 1994 .

[158]  S. Buchwald,et al.  A catalytic method for the reduction of esters to alcohols , 1991 .

[159]  Yitzhak Apeloig,et al.  The chemistry of organic silicon compounds , 1989 .

[160]  Y. Nagai,et al.  Bis(η5-cyclopentadienyl)diphenyltitanium-catalyzed hydrosilylation of ketones , 1988 .

[161]  P. Mencarelli,et al.  INTERACTION OF 3,4-DINITRO-1-METHYLPYRROLE WITH SECONDARY AMINES: ALTERNATIVE FORMATION OF PYRROLINES OR CINE SUBSTITUTION PRODUCTS , 1983 .

[162]  J. Moreau,et al.  Reactions de l'ortho-bis(dimethylsilyl)benzene avec les nitriles catalysees par des complexes du rhodium , 1982 .

[163]  R. Calas Thirty years in organosilicon chemistry , 1980 .

[164]  R. Corriu,et al.  Catalyse heterogene en presence de sels et sans solvant , 1979 .

[165]  M. Kuehne,et al.  Reduction of amides and lactams to amines by reactions with phosphorus oxychloride and sodium borohydride , 1977 .

[166]  N. Langlois,et al.  Reduction asymetrique catalysee par des complexes de metaux de transition IV. synthese d'amines chirales au moyen d'un complexe de rhodium et d'isopropylidene dihydroxy-2,3 bis(diphenylphosphino)-1,4 butane (diop) , 1975 .

[167]  J. Moreau,et al.  Asymmetric synthesis at silicon , 1975 .

[168]  R. Calas Sur Quelques aspects de la reactivite des hydrogenosilanes en chimie organique , 1966 .

[169]  F. Whitmore,et al.  Hydrogen-Halogen Exchange Reactions of Triethylsilane. A New Rearrangement of Neopentyl Chloride1 , 1947 .

[170]  H. Adkins,et al.  Catalytic Hydrogenation of Amides to Amines , 1934 .

[171]  A. Tlili,et al.  Reductive functionalization of CO2 with amines: an entry to formamide, formamidine and methylamine derivatives , 2015 .

[172]  Jean‐Baptiste Sortais,et al.  A convenient nickel-catalysed hydrosilylation of carbonyl derivatives , 2013 .

[173]  S. Enthaler,et al.  Practical One-Pot Synthesis of Secondary Amines by Zinc-Catalyzed Reductive Amination , 2011 .

[174]  A. Papworth,et al.  Selective hydrogenation of amides using Rh/Mo catalysts , 2010 .

[175]  S. Breeden,et al.  Reduction of Carboxylic Esters and Acids by Polymethylhydrosiloxane catalysed by Titanium and Zirconium alkoxides , 1994 .

[176]  T. Murai,et al.  Cobalt carbonyl catalyzed hydrosilylation of nitriles: a new preparation of N,N-disilylamines , 1990 .

[177]  T. Murai,et al.  Cobalt carbonyl catalyzed reduction of aromatic nitriles with a hydrosilane leading to N,N-disilylamines , 1985 .

[178]  R. Corriu,et al.  Reduction selective de composes carbonyles par catalyse heterogene a la surface des sels , 1981 .

[179]  N. Langlois,et al.  Synthese asymetrique d'amines par hydrosilylation d'imines catalysee par un complexe chiral du rhodium , 1973 .