Journal
SCIENCE
Volume 352, Issue 6291, Pages 1304-1308Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aaf6635
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Funding
- NIH National Institute of General Medical Sciences [R01 GM078201-05]
- Bristol-Myers Squibb
- Marie Curie Actions
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The use of sp(3) C-H bonds-which are ubiquitous in organic molecules-as latent nucleophile equivalents for transition metal-catalyzed cross-coupling reactions has the potential to substantially streamline synthetic efforts in organic chemistry while bypassing substrate activation steps. Through the combination of photoredox-mediated hydrogen atom transfer (HAT) and nickel catalysis, we have developed a highly selective and general C-H arylation protocol that activates a wide array of C-H bonds as native functional handles for cross-coupling. This mild approach takes advantage of a tunable HAT catalyst that exhibits predictable reactivity patterns based on enthalpic and bond polarity considerations to selectively functionalize a-amino and a-oxy sp(3) C-H bonds in both cyclic and acyclic systems.
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