TY - JOUR
T1 - Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis
AU - Ackerman, Laura K.G.
AU - Martinez Alvarado, Jesus I.
AU - Doyle, Abigail G.
N1 - Publisher Copyright:
Copyright © 2018 American Chemical Society
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.
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U2 - 10.1021/jacs.8b09191
DO - 10.1021/jacs.8b09191
M3 - Article
C2 - 30351143
AN - SCOPUS:85055121511
SN - 0002-7863
VL - 140
SP - 14059
EP - 14063
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 43
ER -