A Metallaphotoredox Strategy for the Cross-Electrophile Coupling of α-Chloro Carbonyls with Aryl Halides

Tiffany Q. Chen, David W.C. MacMillan

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

Here, we demonstrate that a metallaphotoredox-catalyzed cross-electrophile coupling mechanism provides a unified method for the α-arylation of diverse activated alkyl chlorides, including α-chloroketones, α-chloroesters, α-chloroamides, α-chlorocarboxylic acids, and benzylic chlorides. This strategy, which is effective for a wide variety of aryl bromide coupling partners, is predicated upon a halogen atom abstraction/nickel radical-capture mechanism that is generically successful across an extensive range of carbonyl substrates. The construction and use of arylacetic acid products have further enabled two-step protocols for the delivery of valuable building blocks for medicinal chemistry, such as aryldifluoromethyl and diarylmethane motifs.

Original languageEnglish (US)
Pages (from-to)14584-14588
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number41
DOIs
StatePublished - Oct 7 2019

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • carboxylic acids
  • heterocycles
  • nickel
  • photocatalysis
  • α-arylation

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