General Olefin Synthesis by the Palladium-Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective N-C Activation

Guangrong Meng; Michal Szostak

doi:10.1002/anie.201507776

General Olefin Synthesis by the Palladium-Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective N-C Activation

Guangrong Meng, Michal Szostak

Rutgers Newark, Chemistry

Rutgers, The State University

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

209 Scopus citations

Abstract

Metal-catalyzed reactions of amides proceeding via metal insertion into the N-CO bond are severely underdeveloped due to resonance stabilization of the amide bond. Herein we report the first Heck reaction of amides proceeding via highly chemoselective N-CO cleavage catalyzed by Pd⁰ utilizing amide bond ground-state destabilization. Conceptually, this transformation provides access to a myriad of metal-catalyzed transformations of amides via metal insertion/decarbonylation.

Original language	American English
Pages (from-to)	14518-14522
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	48
DOIs	https://doi.org/10.1002/anie.201507776
State	Published - Nov 23 2015

ASJC Scopus subject areas

Catalysis
General Chemistry

Keywords

Heck reaction
N-C activation
amide bonds
base-free Heck reaction
twisted amides

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10.1002/anie.201507776

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title = "General Olefin Synthesis by the Palladium-Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective N-C Activation",

abstract = "Metal-catalyzed reactions of amides proceeding via metal insertion into the N-CO bond are severely underdeveloped due to resonance stabilization of the amide bond. Herein we report the first Heck reaction of amides proceeding via highly chemoselective N-CO cleavage catalyzed by Pd0 utilizing amide bond ground-state destabilization. Conceptually, this transformation provides access to a myriad of metal-catalyzed transformations of amides via metal insertion/decarbonylation.",

keywords = "Heck reaction, N-C activation, amide bonds, base-free Heck reaction, twisted amides",

author = "Guangrong Meng and Michal Szostak",

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Y1 - 2015/11/23

N2 - Metal-catalyzed reactions of amides proceeding via metal insertion into the N-CO bond are severely underdeveloped due to resonance stabilization of the amide bond. Herein we report the first Heck reaction of amides proceeding via highly chemoselective N-CO cleavage catalyzed by Pd0 utilizing amide bond ground-state destabilization. Conceptually, this transformation provides access to a myriad of metal-catalyzed transformations of amides via metal insertion/decarbonylation.

AB - Metal-catalyzed reactions of amides proceeding via metal insertion into the N-CO bond are severely underdeveloped due to resonance stabilization of the amide bond. Herein we report the first Heck reaction of amides proceeding via highly chemoselective N-CO cleavage catalyzed by Pd0 utilizing amide bond ground-state destabilization. Conceptually, this transformation provides access to a myriad of metal-catalyzed transformations of amides via metal insertion/decarbonylation.

KW - Heck reaction

KW - N-C activation

KW - amide bonds

KW - base-free Heck reaction

KW - twisted amides

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ER -

General Olefin Synthesis by the Palladium-Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective N-C Activation

Abstract

ASJC Scopus subject areas

Keywords

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