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Literature DB >> 25914240

Cobalt-catalyzed hydrogenation of esters to alcohols: unexpected reactivity trend indicates ester enolate intermediacy.

Dipankar Srimani^1,2, Arup Mukherjee¹, Alexander F G Goldberg¹, Gregory Leitus³, Yael Diskin-Posner³, Linda J W Shimon³, Yehoshoa Ben David¹, David Milstein⁴.

Abstract

The atom-efficient and environmentally benign catalytic hydrogenation of carboxylic acid esters to alcohols has been accomplished in recent years mainly with precious-metal-based catalysts, with few exceptions. Presented here is the first cobalt-catalyzed hydrogenation of esters to the corresponding alcohols. Unexpectedly, the evidence indicates the unprecedented involvement of ester enolate intermediates.

Entities: Chemical

Keywords: alcohols; cobalt; esters; homogeneous catalysis; hydrogenation

Mesh：

Substances：

Year: 2015 PMID： 25914240 DOI： 10.1002/anie.201502418

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

15 in total

1. Electro- and Solar-Driven Fuel Synthesis with First Row Transition Metal Complexes.

Authors: Kristian E Dalle; Julien Warnan; Jane J Leung; Bertrand Reuillard; Isabell S Karmel; Erwin Reisner
Journal: Chem Rev Date: 2019-02-15 Impact factor: 60.622

2. CH₂ Linkage Effects on the Reactivity of Bis(aminophosphine)-Ruthenium Complexes for Selective Hydrogenation of Esters into Alcohols.

Authors: Xiaolong Fang; Mingjun Sun; Jianwei Zheng; Bin Li; Linmin Ye; Xiaoping Wang; Zexing Cao; Hongping Zhu; Youzhu Yuan
Journal: Sci Rep Date: 2017-06-21 Impact factor: 4.379

3. Non-Pincer-Type Manganese Complexes as Efficient Catalysts for the Hydrogenation of Esters.

Authors: Robbert van Putten; Evgeny A Uslamin; Marcel Garbe; Chong Liu; Angela Gonzalez-de-Castro; Martin Lutz; Kathrin Junge; Emiel J M Hensen; Matthias Beller; Laurent Lefort; Evgeny A Pidko
Journal: Angew Chem Int Ed Engl Date: 2017-04-21 Impact factor: 15.336

4. Alkene Metalates as Hydrogenation Catalysts.

Authors: Philipp Büschelberger; Dominik Gärtner; Efrain Reyes-Rodriguez; Friedrich Kreyenschmidt; Konrad Koszinowski; Axel Jacobi von Wangelin; Robert Wolf
Journal: Chemistry Date: 2017-02-06 Impact factor: 5.236

5. Efficient and selective hydrogenation of amides to alcohols and amines using a well-defined manganese-PNN pincer complex.

Authors: Veronica Papa; Jose R Cabrero-Antonino; Elisabetta Alberico; Anke Spanneberg; Kathrin Junge; Henrik Junge; Matthias Beller
Journal: Chem Sci Date: 2017-03-08 Impact factor: 9.825

Cobalt-catalyzed hydrogenation of esters to alcohols: unexpected reactivity trend indicates ester enolate intermediacy.

1. Electro- and Solar-Driven Fuel Synthesis with First Row Transition Metal Complexes.

2. CH₂ Linkage Effects on the Reactivity of Bis(aminophosphine)-Ruthenium Complexes for Selective Hydrogenation of Esters into Alcohols.

3. Non-Pincer-Type Manganese Complexes as Efficient Catalysts for the Hydrogenation of Esters.

4. Alkene Metalates as Hydrogenation Catalysts.

5. Efficient and selective hydrogenation of amides to alcohols and amines using a well-defined manganese-PNN pincer complex.

6. Hydrogenation of Polyesters to Polyether Polyols.

7. Selective and Additive-Free Hydrogenation of Nitroarenes Mediated by a DMSO-Tagged Molecular Cobalt Corrole Catalyst.

8. Cobalt-catalysed reductive C-H alkylation of indoles using carboxylic acids and molecular hydrogen.

9. Unprecedented selective homogeneous cobalt-catalysed reductive alkoxylation of cyclic imides under mild conditions.

10. Highly selective hydrogenation of amides catalysed by a molybdenum pincer complex: scope and mechanism.