LiCl-Accelerated multimetallic cross-coupling of aryl chlorides with aryl triflates

Liangbin Huang, Laura K.G. Ackerman, Kai Kang, Astrid M. Parsons, Daniel J. Weix

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

While the synthesis of biaryls has advanced rapidly in the past decades, cross-Ullman couplings of aryl chlorides, the most abundant aryl electrophiles, have remained elusive. Reported here is the first general cross-Ullman coupling of aryl chlorides with aryl triflates. The selectivity challenge associated with coupling an inert electrophile with a reactive one is overcome using a multimetallic strategy with the appropriate choice of additive. Studies demonstrate that LiCl is essential for effective cross-coupling by accelerating the reduction of Ni(II) to Ni(0) and counteracting autoinhibition of reduction at Zn(0) by Zn(II) salts. The modified conditions tolerate a variety of functional groups on either coupling partner (42 examples), and examples include a three-step synthesis of flurbiprofen.

Original languageEnglish (US)
Pages (from-to)10978-10983
Number of pages6
JournalJournal of the American Chemical Society
Volume141
Issue number28
DOIs
StatePublished - Jun 30 2019

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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