ReportOrganic Chemistry

Native functionality in triple catalytic cross-coupling: sp3 C–H bonds as latent nucleophiles

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Science  28 Apr 2016:
aaf6635
DOI: 10.1126/science.aaf6635

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Abstract

The use of sp3 C–H bonds—which are ubiquitous in organic molecules—as latent nucleophile equivalents for transition metal-catalyzed cross-coupling reactions has the potential to dramatically 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 α-amino and α-oxy sp3 C–H bonds in both cyclic and acyclic systems.

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