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

Megan H. Shaw, Valerie W. Shurtleff, Jack A. Terrett, James D. Cuthbertson, David W.C. MacMillan

Research output: Contribution to journalArticle

234 Scopus citations

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 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 α-amino and α-oxy sp3 C-H bonds in both cyclic and acyclic systems.

Original languageEnglish (US)
Pages (from-to)1304-1308
Number of pages5
JournalScience
Volume352
Issue number6291
DOIs
StatePublished - Jun 10 2016

All Science Journal Classification (ASJC) codes

  • General

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