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.
Ackerman, L. K. G.; Martinez Alvarado, J. I.; Doyle, A. G. Direct C−C Bond Formation from Alkanes Using Ni and Photoredox Catalysis. J. Am. Chem. Soc. 2018,140, 14059-1406