Journal
SCIENCE
Volume 360, Issue 6392, Pages 1010-+Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aat4133
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Funding
- NIH National Institute of General Medical Sciences [R01 GM103558-03]
- Bristol-Myers Squibb
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM103558] Funding Source: NIH RePORTER
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Transition metal-catalyzed arene functionalization has been widely used for molecular synthesis over the past century. In this arena, copper catalysis has long been considered a privileged platform due to the propensity of high-valent copper to undergo reductive elimination with a wide variety of coupling fragments. However, the sluggish nature of oxidative addition has limited copper's capacity to broadly facilitate haloarene coupling protocols. Here, we demonstrate that this copper oxidative addition problem can be overcome with an aryl radical-capture mechanism, wherein the aryl radical is generated through a silyl radical halogen abstraction. This strategy was applied to a general trifluoromethylation of aryl bromides through dual copper-photoredox catalysis. Mechanistic studies support the formation of an open-shell aryl species.
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