Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 39, Pages 12715-12718Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b04789
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Funding
- NIGMS [R01-GM-113878]
- NSF [CHE-1362841]
- Bristol-Myers Squibb Graduate Fellowship
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An iridium photocatalyst and visible light facilitate a room temperature, nickel-catalyzed coupling of (hetero)aryl bromides with activated alpha-heterosubstituted or benzylic C(sp(3))-H bonds. Mechanistic investigations on this unprecedented transformation have uncovered the possibility of an unexpected mechanism hypothesized to involve a Ni-Br homolysis event from an excited-state nickel complex. The resultant bromine radical is thought to abstract weak C(sp(3))-H bonds to generate reactive alkyl radicals that can be engaged in Ni-catalyzed arylation. Evidence suggests that the iridium photocatalyst facilitates nickel excitation and bromine radical generation via triplet-triplet energy transfer.
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