Cobalt-Catalyzed Hydrogenation of Esters to Alcohols: Unexpected Reactivity Trend Indicates Ester Enolate Intermediacy

Dipankar Srimani, Arup Mukherjee, Alexander F G Goldberg, Gregory Leitus, Yael Diskin-Posner, Linda J W Shimon, Yehoshoa Ben David, David Milstein

Research output: Contribution to journalArticle

92 Citations (Scopus)

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. Getting involved: 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. Presented here is the first cobalt-catalyzed hydrogenation of esters to alcohols. Unexpectedly, the evidence indicates the unprecedented involvement of ester enolate intermediates.

Original languageEnglish
Pages (from-to)12357-12360
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number42
DOIs
Publication statusPublished - Oct 1 2015

Fingerprint

Cobalt
Hydrogenation
Esters
Alcohols
Precious metals
Carboxylic Acids
Carboxylic acids
Atoms
Catalysts

Keywords

  • alcohols
  • cobalt
  • esters
  • homogeneous catalysis
  • hydrogenation

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Cobalt-Catalyzed Hydrogenation of Esters to Alcohols : Unexpected Reactivity Trend Indicates Ester Enolate Intermediacy. / Srimani, Dipankar; Mukherjee, Arup; Goldberg, Alexander F G; Leitus, Gregory; Diskin-Posner, Yael; Shimon, Linda J W; Ben David, Yehoshoa; Milstein, David.

In: Angewandte Chemie - International Edition, Vol. 54, No. 42, 01.10.2015, p. 12357-12360.

Research output: Contribution to journalArticle

Srimani, D, Mukherjee, A, Goldberg, AFG, Leitus, G, Diskin-Posner, Y, Shimon, LJW, Ben David, Y & Milstein, D 2015, 'Cobalt-Catalyzed Hydrogenation of Esters to Alcohols: Unexpected Reactivity Trend Indicates Ester Enolate Intermediacy', Angewandte Chemie - International Edition, vol. 54, no. 42, pp. 12357-12360. https://doi.org/10.1002/anie.201502418
Srimani, Dipankar ; Mukherjee, Arup ; Goldberg, Alexander F G ; Leitus, Gregory ; Diskin-Posner, Yael ; Shimon, Linda J W ; Ben David, Yehoshoa ; Milstein, David. / Cobalt-Catalyzed Hydrogenation of Esters to Alcohols : Unexpected Reactivity Trend Indicates Ester Enolate Intermediacy. In: Angewandte Chemie - International Edition. 2015 ; Vol. 54, No. 42. pp. 12357-12360.
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