Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 43, Pages 14059-14063Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b09191
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Funding
- NIGMS [R01 GM100985, R35 GM126986]
- F32 Ruth L Kirschtein NRSA Fellowship [5 F32 GM119364-02]
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A method for direct cross coupling between unactivated C(sp(3))-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.
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