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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.

SUBMITTER: Ackerman LKG

PROVIDER: S-EPMC6411045 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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

Ackerman Laura K G LKG Martinez Alvarado Jesus I JI Doyle Abigail G AG

Journal of the American Chemical Society 20181016 43

A method for direct cross coupling between unactivated C(sp<sup>3</sup>)-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 ...[more]

PMID: 30351143

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