Unprecedented iron-catalyzed ester hydrogenation. Mild, selective, and efficient hydrogenation of trifluoroacetic esters to alcohols catalyzed by an iron pincer complex

Thomas Zell, Yehoshoa Ben-David, David Milstein

Research output: Contribution to journalArticle

127 Citations (Scopus)

Abstract

The synthetically important, environmentally benign hydrogenation of esters to alcohols has been accomplished in recent years only with precious-metal-based catalysts. Here we present the first iron-catalyzed hydrogenation of esters to the corresponding alcohols, proceeding selectively and efficiently in the presence of an iron pincer catalyst under remarkably mild conditions. The replacement of precious-metal catalysts by an iron complex was accomplished for the synthetically important, environmentally benign hydrogenation of esters to alcohols under mild conditions. The iron pincer complex (see scheme) selectively and efficiently catalyzes the hydrogenation of trifluoroacetates under remarkably mild conditions (5-25 bar and 40 °C).

Original languageEnglish
Pages (from-to)4685-4689
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number18
DOIs
Publication statusPublished - Apr 25 2014

Fingerprint

Hydrogenation
Esters
Alcohols
Iron
Precious metals
Catalysts
Trifluoroacetic Acid

Keywords

  • esters
  • homogenous catalysis
  • hydrogenation
  • iron complexes
  • pincer ligands

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

@article{eeb91bfe8c294d23b29ca60963235784,
title = "Unprecedented iron-catalyzed ester hydrogenation. Mild, selective, and efficient hydrogenation of trifluoroacetic esters to alcohols catalyzed by an iron pincer complex",
abstract = "The synthetically important, environmentally benign hydrogenation of esters to alcohols has been accomplished in recent years only with precious-metal-based catalysts. Here we present the first iron-catalyzed hydrogenation of esters to the corresponding alcohols, proceeding selectively and efficiently in the presence of an iron pincer catalyst under remarkably mild conditions. The replacement of precious-metal catalysts by an iron complex was accomplished for the synthetically important, environmentally benign hydrogenation of esters to alcohols under mild conditions. The iron pincer complex (see scheme) selectively and efficiently catalyzes the hydrogenation of trifluoroacetates under remarkably mild conditions (5-25 bar and 40 °C).",
keywords = "esters, homogenous catalysis, hydrogenation, iron complexes, pincer ligands",
author = "Thomas Zell and Yehoshoa Ben-David and David Milstein",
year = "2014",
month = "4",
day = "25",
doi = "10.1002/anie.201311221",
language = "English",
volume = "53",
pages = "4685--4689",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "18",

}

TY - JOUR

T1 - Unprecedented iron-catalyzed ester hydrogenation. Mild, selective, and efficient hydrogenation of trifluoroacetic esters to alcohols catalyzed by an iron pincer complex

AU - Zell, Thomas

AU - Ben-David, Yehoshoa

AU - Milstein, David

PY - 2014/4/25

Y1 - 2014/4/25

N2 - The synthetically important, environmentally benign hydrogenation of esters to alcohols has been accomplished in recent years only with precious-metal-based catalysts. Here we present the first iron-catalyzed hydrogenation of esters to the corresponding alcohols, proceeding selectively and efficiently in the presence of an iron pincer catalyst under remarkably mild conditions. The replacement of precious-metal catalysts by an iron complex was accomplished for the synthetically important, environmentally benign hydrogenation of esters to alcohols under mild conditions. The iron pincer complex (see scheme) selectively and efficiently catalyzes the hydrogenation of trifluoroacetates under remarkably mild conditions (5-25 bar and 40 °C).

AB - The synthetically important, environmentally benign hydrogenation of esters to alcohols has been accomplished in recent years only with precious-metal-based catalysts. Here we present the first iron-catalyzed hydrogenation of esters to the corresponding alcohols, proceeding selectively and efficiently in the presence of an iron pincer catalyst under remarkably mild conditions. The replacement of precious-metal catalysts by an iron complex was accomplished for the synthetically important, environmentally benign hydrogenation of esters to alcohols under mild conditions. The iron pincer complex (see scheme) selectively and efficiently catalyzes the hydrogenation of trifluoroacetates under remarkably mild conditions (5-25 bar and 40 °C).

KW - esters

KW - homogenous catalysis

KW - hydrogenation

KW - iron complexes

KW - pincer ligands

UR - http://www.scopus.com/inward/record.url?scp=84899498172&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84899498172&partnerID=8YFLogxK

U2 - 10.1002/anie.201311221

DO - 10.1002/anie.201311221

M3 - Article

AN - SCOPUS:84899498172

VL - 53

SP - 4685

EP - 4689

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 18

ER -