Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis

Laura K.G. Ackerman; Jesus I. Martinez Alvarado; Abigail G. Doyle

doi:10.1021/jacs.8b09191

Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis

Laura K.G. Ackerman
, Jesus I. Martinez Alvarado
, Abigail G. Doyle

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

225 Scopus citations

Abstract

A method for direct cross coupling between unactivated C(sp³)-H bonds and chloroformates has been accomplished via nickel and photoredox catalysis. A diverse range of feedstock chemicals, such as (a)cyclic alkanes and toluenes, along with late-stage intermediates, undergo intermolecular C-C bond formation to afford esters under mild conditions using only 3 equiv of the C-H partner. Site selectivity is predictable according to bond strength and polarity trends that are consistent with the intermediacy of a chlorine radical as the hydrogen atom-abstracting species.

Original language	English (US)
Pages (from-to)	14059-14063
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	140
Issue number	43
DOIs	https://doi.org/10.1021/jacs.8b09191
State	Published - Oct 31 2018

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.8b09191

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title = "Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis",

abstract = "A method for direct cross coupling between unactivated C(sp3)-H bonds and chloroformates has been accomplished via nickel and photoredox catalysis. A diverse range of feedstock chemicals, such as (a)cyclic alkanes and toluenes, along with late-stage intermediates, undergo intermolecular C-C bond formation to afford esters under mild conditions using only 3 equiv of the C-H partner. Site selectivity is predictable according to bond strength and polarity trends that are consistent with the intermediacy of a chlorine radical as the hydrogen atom-abstracting species.",

author = "Ackerman, \{Laura K.G.\} and \{Martinez Alvarado\}, \{Jesus I.\} and Doyle, \{Abigail G.\}",

note = "Publisher Copyright: Copyright {\textcopyright} 2018 American Chemical Society",

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doi = "10.1021/jacs.8b09191",

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AU - Ackerman, Laura K.G.

AU - Martinez Alvarado, Jesus I.

AU - Doyle, Abigail G.

PY - 2018/10/31

Y1 - 2018/10/31

N2 - A method for direct cross coupling between unactivated C(sp3)-H bonds and chloroformates has been accomplished via nickel and photoredox catalysis. A diverse range of feedstock chemicals, such as (a)cyclic alkanes and toluenes, along with late-stage intermediates, undergo intermolecular C-C bond formation to afford esters under mild conditions using only 3 equiv of the C-H partner. Site selectivity is predictable according to bond strength and polarity trends that are consistent with the intermediacy of a chlorine radical as the hydrogen atom-abstracting species.

AB - A method for direct cross coupling between unactivated C(sp3)-H bonds and chloroformates has been accomplished via nickel and photoredox catalysis. A diverse range of feedstock chemicals, such as (a)cyclic alkanes and toluenes, along with late-stage intermediates, undergo intermolecular C-C bond formation to afford esters under mild conditions using only 3 equiv of the C-H partner. Site selectivity is predictable according to bond strength and polarity trends that are consistent with the intermediacy of a chlorine radical as the hydrogen atom-abstracting species.

UR - https://www.scopus.com/pages/publications/85055121511

UR - https://www.scopus.com/pages/publications/85055121511#tab=citedBy

U2 - 10.1021/jacs.8b09191

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AN - SCOPUS:85055121511

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 43

ER -

Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis

Abstract

All Science Journal Classification (ASJC) codes

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