Direct Conversion of Alcohols into Alkenes by Dehydrogenative Coupling with Hydrazine/Hydrazone Catalyzed by Manganese

Uttam Kumar Das, Subrata Chakraborty, Yael Diskin-Posner, David Milstein

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

We have developed unprecedented methods for the direct transformation of primary alcohols to alkenes in the presence of hydrazine, and for the synthesis of mixed alkenes by the reaction of alcohols with hydrazones. The reactions are catalyzed by a manganese pincer complex and proceed in absence of added base or hydrogen acceptors, liberating dihydrogen, dinitrogen, and water as the only byproducts. The proposed mechanism, based on preparation of proposed intermediates and control experiments, suggests that the transformation occurs through metal–ligand cooperative N−H activation of a hydrazone intermediate.

Original languageEnglish
Pages (from-to)13444-13448
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number41
DOIs
Publication statusPublished - Oct 8 2018

Fingerprint

hydrazine
Hydrazones
Hydrazine
Alkenes
Manganese
Olefins
Alcohols
Byproducts
Hydrogen
Chemical activation
Water
Experiments

Keywords

  • alcohols
  • dehydrogenative coupling
  • homogeneous catalysis
  • hydrazines
  • manganese

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Direct Conversion of Alcohols into Alkenes by Dehydrogenative Coupling with Hydrazine/Hydrazone Catalyzed by Manganese. / Das, Uttam Kumar; Chakraborty, Subrata; Diskin-Posner, Yael; Milstein, David.

In: Angewandte Chemie - International Edition, Vol. 57, No. 41, 08.10.2018, p. 13444-13448.

Research output: Contribution to journalArticle

@article{68b340dc8c6043b7843bd3ae1aaa54b5,
title = "Direct Conversion of Alcohols into Alkenes by Dehydrogenative Coupling with Hydrazine/Hydrazone Catalyzed by Manganese",
abstract = "We have developed unprecedented methods for the direct transformation of primary alcohols to alkenes in the presence of hydrazine, and for the synthesis of mixed alkenes by the reaction of alcohols with hydrazones. The reactions are catalyzed by a manganese pincer complex and proceed in absence of added base or hydrogen acceptors, liberating dihydrogen, dinitrogen, and water as the only byproducts. The proposed mechanism, based on preparation of proposed intermediates and control experiments, suggests that the transformation occurs through metal–ligand cooperative N−H activation of a hydrazone intermediate.",
keywords = "alcohols, dehydrogenative coupling, homogeneous catalysis, hydrazines, manganese",
author = "Das, {Uttam Kumar} and Subrata Chakraborty and Yael Diskin-Posner and David Milstein",
year = "2018",
month = "10",
day = "8",
doi = "10.1002/anie.201807881",
language = "English",
volume = "57",
pages = "13444--13448",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "41",

}

TY - JOUR

T1 - Direct Conversion of Alcohols into Alkenes by Dehydrogenative Coupling with Hydrazine/Hydrazone Catalyzed by Manganese

AU - Das, Uttam Kumar

AU - Chakraborty, Subrata

AU - Diskin-Posner, Yael

AU - Milstein, David

PY - 2018/10/8

Y1 - 2018/10/8

N2 - We have developed unprecedented methods for the direct transformation of primary alcohols to alkenes in the presence of hydrazine, and for the synthesis of mixed alkenes by the reaction of alcohols with hydrazones. The reactions are catalyzed by a manganese pincer complex and proceed in absence of added base or hydrogen acceptors, liberating dihydrogen, dinitrogen, and water as the only byproducts. The proposed mechanism, based on preparation of proposed intermediates and control experiments, suggests that the transformation occurs through metal–ligand cooperative N−H activation of a hydrazone intermediate.

AB - We have developed unprecedented methods for the direct transformation of primary alcohols to alkenes in the presence of hydrazine, and for the synthesis of mixed alkenes by the reaction of alcohols with hydrazones. The reactions are catalyzed by a manganese pincer complex and proceed in absence of added base or hydrogen acceptors, liberating dihydrogen, dinitrogen, and water as the only byproducts. The proposed mechanism, based on preparation of proposed intermediates and control experiments, suggests that the transformation occurs through metal–ligand cooperative N−H activation of a hydrazone intermediate.

KW - alcohols

KW - dehydrogenative coupling

KW - homogeneous catalysis

KW - hydrazines

KW - manganese

UR - http://www.scopus.com/inward/record.url?scp=85053035341&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85053035341&partnerID=8YFLogxK

U2 - 10.1002/anie.201807881

DO - 10.1002/anie.201807881

M3 - Article

VL - 57

SP - 13444

EP - 13448

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 41

ER -