Dehydrogenative Cross-Coupling of Primary Alcohols To Form Cross-Esters Catalyzed by a Manganese Pincer Complex

Uttam Kumar Das; Yehoshoa Ben-David; Gregory Leitus; Yael Diskin-Posner; David Milstein

doi:10.1021/acscatal.8b04585

Dehydrogenative Cross-Coupling of Primary Alcohols To Form Cross-Esters Catalyzed by a Manganese Pincer Complex

Uttam Kumar Das, Yehoshoa Ben-David, Gregory Leitus, Yael Diskin-Posner, David Milstein^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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Abstract

Base-metal-catalyzed dehydrogenative cross-coupling of primary alcohols to form cross-esters as major products, liberating hydrogen gas, is reported. The reaction is catalyzed by a pincer complex of earth-abundant manganese in the presence of catalytic base, without any hydrogen acceptor or oxidant. Mechanistic insight indicates that a dearomatized complex is the actual catalyst, and indeed this independently prepared dearomatized complex catalyzes the reaction under neutral conditions.

Original language	English
Pages (from-to)	479-484
Number of pages	6
Journal	ACS Catalysis
Volume	9
Issue number	1
DOIs	https://doi.org/10.1021/acscatal.8b04585
Publication status	Published - 4 Jan 2019

Funding

This research was supported by the European Research Council (ERC AdG 692775). D.M. holds the Israel Matz Professorial Chair of Organic Chemistry. U.K.D. is thankful to The Science & Engineering Research Board (SERB), DST, and Govt. of India for the SERB Overseas Postdoctoral Fellowship.

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

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10.1021/acscatal.8b04585

dm_ACS_dehydrogenativeCrossCoupling_AM2019Accepted author manuscript, 866 KBLicence: Unspecified

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abstract = "Base-metal-catalyzed dehydrogenative cross-coupling of primary alcohols to form cross-esters as major products, liberating hydrogen gas, is reported. The reaction is catalyzed by a pincer complex of earth-abundant manganese in the presence of catalytic base, without any hydrogen acceptor or oxidant. Mechanistic insight indicates that a dearomatized complex is the actual catalyst, and indeed this independently prepared dearomatized complex catalyzes the reaction under neutral conditions.",

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AU - Leitus, Gregory

AU - Diskin-Posner, Yael

AU - Milstein, David

PY - 2019/1/4

Y1 - 2019/1/4

N2 - Base-metal-catalyzed dehydrogenative cross-coupling of primary alcohols to form cross-esters as major products, liberating hydrogen gas, is reported. The reaction is catalyzed by a pincer complex of earth-abundant manganese in the presence of catalytic base, without any hydrogen acceptor or oxidant. Mechanistic insight indicates that a dearomatized complex is the actual catalyst, and indeed this independently prepared dearomatized complex catalyzes the reaction under neutral conditions.

AB - Base-metal-catalyzed dehydrogenative cross-coupling of primary alcohols to form cross-esters as major products, liberating hydrogen gas, is reported. The reaction is catalyzed by a pincer complex of earth-abundant manganese in the presence of catalytic base, without any hydrogen acceptor or oxidant. Mechanistic insight indicates that a dearomatized complex is the actual catalyst, and indeed this independently prepared dearomatized complex catalyzes the reaction under neutral conditions.

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Dehydrogenative Cross-Coupling of Primary Alcohols To Form Cross-Esters Catalyzed by a Manganese Pincer Complex

Abstract

Funding

All Science Journal Classification (ASJC) codes

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