Merging photoredox and nickel catalysis: Decarboxylative cross-coupling of carboxylic acids with vinyl halides

Adam Noble; Stefan J. McCarver; David W.C. Macmillan

doi:10.1021/ja511913h

Merging photoredox and nickel catalysis: Decarboxylative cross-coupling of carboxylic acids with vinyl halides

Adam Noble, Stefan J. McCarver, David W.C. Macmillan

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

381 Scopus citations

Abstract

Decarboxylative cross-coupling of alkyl carboxylic acids with vinyl halides has been accomplished through the synergistic merger of photoredox and nickel catalysis. This new methodology has been successfully applied to a variety of α-oxy and α-amino acids, as well as simple hydrocarbon-substituted acids. Diverse vinyl iodides and bromides give rise to vinylation products in high efficiency under mild, operationally simple reaction conditions.

Original language	English (US)
Pages (from-to)	624-627
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	2
DOIs	https://doi.org/10.1021/ja511913h
State	Published - Jan 21 2015

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja511913h

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title = "Merging photoredox and nickel catalysis: Decarboxylative cross-coupling of carboxylic acids with vinyl halides",

abstract = "Decarboxylative cross-coupling of alkyl carboxylic acids with vinyl halides has been accomplished through the synergistic merger of photoredox and nickel catalysis. This new methodology has been successfully applied to a variety of α-oxy and α-amino acids, as well as simple hydrocarbon-substituted acids. Diverse vinyl iodides and bromides give rise to vinylation products in high efficiency under mild, operationally simple reaction conditions.",

author = "Adam Noble and McCarver, {Stefan J.} and Macmillan, {David W.C.}",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2015",

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AU - McCarver, Stefan J.

AU - Macmillan, David W.C.

PY - 2015/1/21

Y1 - 2015/1/21

N2 - Decarboxylative cross-coupling of alkyl carboxylic acids with vinyl halides has been accomplished through the synergistic merger of photoredox and nickel catalysis. This new methodology has been successfully applied to a variety of α-oxy and α-amino acids, as well as simple hydrocarbon-substituted acids. Diverse vinyl iodides and bromides give rise to vinylation products in high efficiency under mild, operationally simple reaction conditions.

AB - Decarboxylative cross-coupling of alkyl carboxylic acids with vinyl halides has been accomplished through the synergistic merger of photoredox and nickel catalysis. This new methodology has been successfully applied to a variety of α-oxy and α-amino acids, as well as simple hydrocarbon-substituted acids. Diverse vinyl iodides and bromides give rise to vinylation products in high efficiency under mild, operationally simple reaction conditions.

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Merging photoredox and nickel catalysis: Decarboxylative cross-coupling of carboxylic acids with vinyl halides

Abstract

All Science Journal Classification (ASJC) codes

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