Three-Component Visible-Light-Induced Palladium-Catalyzed 1,2-Alkyl Carbamoylation/Cyanation of Alkenes

Xiangqing Jia; Ziyan Zhang; Vladimir Gevorgyan

doi:10.1021/acscatal.1c04183

Three-Component Visible-Light-Induced Palladium-Catalyzed 1,2-Alkyl Carbamoylation/Cyanation of Alkenes

Xiangqing Jia, Ziyan Zhang, Vladimir Gevorgyan

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

19 Scopus citations

Abstract

A mild visible-light-induced Pd-catalyzed one-pot three-component alkyl-carbamoylation and cyanation of alkenes was developed. This general transformation, which proceeds via the in situ formation of a reactive ketenimine intermediate, allows for a rapid construction of a broad range of valuable amides and nitriles from readily available alkenes, alkyl iodides, and isocyanides. An efficient synthesis of tetrazole and amidine via this approach was also demonstrated.

Original language	English (US)
Pages (from-to)	13217-13222
Number of pages	6
Journal	ACS Catalysis
Volume	11
Issue number	21
DOIs	https://doi.org/10.1021/acscatal.1c04183
State	Published - Nov 5 2021

Keywords

difunctionalization
isocyanide
light-induced
palladium
radical

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1021/acscatal.1c04183

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title = "Three-Component Visible-Light-Induced Palladium-Catalyzed 1,2-Alkyl Carbamoylation/Cyanation of Alkenes",

abstract = "A mild visible-light-induced Pd-catalyzed one-pot three-component alkyl-carbamoylation and cyanation of alkenes was developed. This general transformation, which proceeds via the in situ formation of a reactive ketenimine intermediate, allows for a rapid construction of a broad range of valuable amides and nitriles from readily available alkenes, alkyl iodides, and isocyanides. An efficient synthesis of tetrazole and amidine via this approach was also demonstrated.",

keywords = "difunctionalization, isocyanide, light-induced, palladium, radical",

author = "Xiangqing Jia and Ziyan Zhang and Vladimir Gevorgyan",

note = "Funding Information: We thank the National Institutes of Health (GM120281), National Science Foundation (CHE-1955663), and Welch Foundation (Chair, AT-0041) for financial support. Publisher Copyright: {\textcopyright} 2021 American Chemical Society",

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doi = "10.1021/acscatal.1c04183",

language = "English (US)",

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T1 - Three-Component Visible-Light-Induced Palladium-Catalyzed 1,2-Alkyl Carbamoylation/Cyanation of Alkenes

AU - Jia, Xiangqing

AU - Zhang, Ziyan

AU - Gevorgyan, Vladimir

N1 - Funding Information: We thank the National Institutes of Health (GM120281), National Science Foundation (CHE-1955663), and Welch Foundation (Chair, AT-0041) for financial support. Publisher Copyright: © 2021 American Chemical Society

PY - 2021/11/5

Y1 - 2021/11/5

N2 - A mild visible-light-induced Pd-catalyzed one-pot three-component alkyl-carbamoylation and cyanation of alkenes was developed. This general transformation, which proceeds via the in situ formation of a reactive ketenimine intermediate, allows for a rapid construction of a broad range of valuable amides and nitriles from readily available alkenes, alkyl iodides, and isocyanides. An efficient synthesis of tetrazole and amidine via this approach was also demonstrated.

AB - A mild visible-light-induced Pd-catalyzed one-pot three-component alkyl-carbamoylation and cyanation of alkenes was developed. This general transformation, which proceeds via the in situ formation of a reactive ketenimine intermediate, allows for a rapid construction of a broad range of valuable amides and nitriles from readily available alkenes, alkyl iodides, and isocyanides. An efficient synthesis of tetrazole and amidine via this approach was also demonstrated.

KW - difunctionalization

KW - isocyanide

KW - light-induced

KW - palladium

KW - radical

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Three-Component Visible-Light-Induced Palladium-Catalyzed 1,2-Alkyl Carbamoylation/Cyanation of Alkenes

Abstract

Keywords

ASJC Scopus subject areas

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