Cyclopentadienone Iron Tricarbonyl Complexes-Catalyzed Hydrogen Transfer in Water

The development of efficient and low-cost catalytic systems is important for the replacement of robust noble metal complexes. The synthesis and application of a stable, phosphine-free, water-soluble cyclopentadienone iron tricarbonyl complex in the reduction of polarized double bonds in pure water is reported. In the presence of cationic bifunctional iron complexes, a variety of alcohols and amines were prepared in good yields under mild reaction conditions.

[1]  Sébastien Coufourier,et al.  Hydrogenation of CO2, Hydrogenocarbonate, and Carbonate to Formate in Water using Phosphine Free Bifunctional Iron Complexes , 2020 .

[2]  J. Renaud,et al.  Iron-Catalyzed β-Alkylation of Alcohols. , 2019, Organic letters.

[3]  Louis C. Morrill,et al.  One-Pot Conversion of Allylic Alcohols to α-Methyl Ketones via Iron-Catalyzed Isomerization–Methylation , 2019, Organic letters.

[4]  Louis C. Morrill,et al.  Iron-Catalyzed Borrowing Hydrogen β-C(sp3)-Methylation of Alcohols , 2019, ACS catalysis.

[5]  A. Poater,et al.  Room-Temperature Chemoselective Reductive Alkylation of Amines Catalyzed by a Well-Defined Iron(II) Complex Using Hydrogen. , 2019, The Journal of organic chemistry.

[6]  Louis C. Morrill,et al.  Iron‐Catalyzed Borrowing Hydrogen C‐Alkylation of Oxindoles with Alcohols , 2019, ChemSusChem.

[7]  M. D. Mbaye,et al.  Iron-Catalyzed Tandem Three-Component Alkylation: Access to α-Methylated Substituted Ketones. , 2019, Organic letters.

[8]  C. Serre,et al.  A MOF-assisted phosphine free bifunctional iron complex for the hydrogenation of carbon dioxide, sodium bicarbonate and carbonate to formate. , 2019, Chemical communications.

[9]  Qiang Liu,et al.  Hydride Transfer Reactions Catalyzed by Cobalt Complexes. , 2019, Chemical reviews.

[10]  C. Darcel,et al.  Iron Catalysis in Reduction and Hydrometalation Reactions. , 2018, Chemical reviews.

[11]  M. D. Mbaye,et al.  Bifunctional Iron Complexes Catalyzed Alkylation of Indoles , 2018, Advanced Synthesis & Catalysis.

[12]  A. Poater,et al.  Well-Defined Phosphine-Free Iron-Catalyzed N-Ethylation and N-Methylation of Amines with Ethanol and Methanol. , 2018, Organic letters.

[13]  M. Beller,et al.  Cobalt Complexes as an Emerging Class of Catalysts for Homogeneous Hydrogenations. , 2018, Accounts of chemical research.

[14]  Louis C. Morrill,et al.  Iron-Catalyzed Methylation Using the Borrowing Hydrogen Approach , 2018, ACS Catalysis.

[15]  A. Poater,et al.  Iron-Catalyzed Chemoselective Reduction of α,β-Unsaturated Ketones. , 2018, Chemistry.

[16]  E. Hensen,et al.  Catalytic (de)hydrogenation promoted by non-precious metals - Co, Fe and Mn: recent advances in an emerging field. , 2018, Chemical Society reviews.

[17]  M. D. Mbaye,et al.  Alkylation of Ketones Catalyzed by Bifunctional Iron Complexes: From Mechanistic Understanding to Application , 2017 .

[18]  Dong Wang,et al.  The golden age of transfer hydrogenation. , 2015, Chemical reviews.

[19]  F. Salehian,et al.  Recent Advances in Reductive Amination Catalysis and Its Applications , 2015 .

[20]  A. Poater,et al.  Highly active phosphine-free bifunctional iron complex for hydrogenation of bicarbonate and reductive amination. , 2015, Chemistry.

[21]  E. Koroleva,et al.  New potential of the reductive alkylation of amines , 2015 .

[22]  L. Cavallo,et al.  Bifunctional (cyclopentadienone)iron-tricarbonyl complexes: synthesis, computational studies and application in reductive amination. , 2013, Chemistry.

[23]  J. Renaud,et al.  Bifunctional Iron Complexes: Efficient Catalysts for CO and CN Reduction in Water , 2013 .

[24]  M. D. Mbaye,et al.  Knölker's iron complex: an efficient in situ generated catalyst for reductive amination of alkyl aldehydes and amines. , 2012, Angewandte Chemie.

[25]  Taylor N. Plank,et al.  Air-Stable, Nitrile-Ligated (Cyclopentadienone)iron Dicarbonyl Compounds as Transfer Reduction and Oxidation Catalysts , 2012 .

[26]  Takahiro Matsumoto,et al.  The development of aqueous transfer hydrogenation catalysts. , 2011, Dalton transactions.

[27]  M. Beller,et al.  An easy and general iron-catalyzed reductive amination of aldehydes and ketones with anilines. , 2011, Chemistry, an Asian journal.

[28]  G. Clarkson,et al.  (Cyclopentadienone)iron Shvo Complexes: Synthesis and Applications to Hydrogen Transfer Reactions , 2011 .

[29]  Timothy W. Funk,et al.  Air-stable iron catalyst for the Oppenauer-type oxidation of alcohols , 2010 .

[30]  T. Nugent,et al.  Chiral Amine Synthesis – Recent Developments and Trends for Enamide Reduction, Reductive Amination, and Imine Reduction , 2010 .

[31]  Jianliang Xiao,et al.  Broader, greener, and more efficient: recent advances in asymmetric transfer hydrogenation. , 2008, Chemistry, an Asian journal.

[32]  B. Bhanage,et al.  Direct Reductive Amination of Carbonyl Compounds with Primary/Secondary Amines Using Recyclable Water‐Soluble FeII/EDTA Complex as Catalyst. , 2008 .

[33]  B. Bhanage,et al.  Direct reductive amination of carbonyl compounds with primary/secondary amines using recyclable water-soluble FeII/EDTA complex as catalyst , 2008 .

[34]  F. Klingler.  Asymmetric hydrogenation of prochiral amino ketones to amino alcohols for pharmaceutical use. , 2007, Accounts of chemical research.

[35]  C Scott Shultz,et al.  Unlocking the potential of asymmetric hydrogenation at Merck. , 2007, Accounts of chemical research.

[36]  L. Saudan,et al.  Hydrogenation processes in the synthesis of perfumery ingredients. , 2007, Accounts of chemical research.

[37]  Paul H. Moran,et al.  Industrial-scale synthesis and applications of asymmetric hydrogenation catalysts. , 2007, Accounts of chemical research.

[38]  B. Pugin,et al.  From a chiral switch to a ligand portfolio for asymmetric catalysis. , 2007, Accounts of chemical research.

[39]  H. Blaser,et al.  Cinchona-modified platinum catalysts: from ligand acceleration to technical processes. , 2007, Accounts of chemical research.

[40]  Takao Saito,et al.  Developments in asymmetric hydrogenation from an industrial perspective. , 2007, Accounts of chemical research.

[41]  G. Grasa,et al.  [(Bisphosphine) Ru(II) diamine] complexes in asymmetric hydrogenation: expanding the scope of the diamine ligand. , 2007, Accounts of chemical research.

[42]  Jianliang Xiao,et al.  Aqueous-phase asymmetric transfer hydrogenation of ketones--a greener approach to chiral alcohols. , 2007, Chemical communications.

[43]  S. Mehrman,et al.  A Review on the Use of Sodium Triacetoxyborohydride in the Reductive Amination of Ketones and Aldehydes , 2006 .

[44]  Ulf M Lindström,et al.  Stereoselective organic reactions in water. , 2002, Chemical reviews.

[45]  H. Goesmann,et al.  Demetalation of Tricarbonyl(cyclopentadienone)iron Complexes Initiated by a Ligand Exchange Reaction with NaOH-X-Ray Analysis of a Complex with Nearly Square-Planar Coordinated Sodium. , 1999, Angewandte Chemie.

[46]  H. Goesmann,et al.  A Novel Method for the Demetalation of Tricarbonyliron-Diene Complexes by a Photolytically Induced Ligand Exchange Reaction with Acetonitrile. , 1999, Angewandte Chemie.

[47]  Wolfgang A. Herrmann,et al.  Aqueous‐Phase Organometallic Catalysis , 1999 .

[48]  H. Knölker.  TRIMETHYLAMINE N-OXIDE : A USEFUL OXIDIZING REAGENT , 1996 .

[49]  H. Knölker,et al.  Transition Metal-Diene Complexes in Organic Synthesis, Part 25.1 Cycloadditions of Annulated 2,5-Bis(trimethylsilyl)cyclopentadienones , 1995 .

[50]  H. Knölker,et al.  Transition Metal-Diene Complexes in Organic Synthesis, Part 18.1 Iron-Mediated [2+2+1] Cycloadditions of Diynes and Carbon Monoxide: Selective Demetalation Reactions , 1994 .

[51]  T. Luh.  Trimethylamine N-oxide—a versatile reagent for organometallic chemistry , 1984 .