Direct catalytic cross-coupling of organolithium compounds

Massimo Giannerini*, Martin Fananas Mastral, Ben L. Feringa

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

147 Citations (Scopus)
1492 Downloads (Pure)

Abstract

Catalytic carbon-carbon bond formation based on cross-coupling reactions plays a central role in the production of natural products, pharmaceuticals, agrochemicals and organic materials. Coupling reactions of a variety of organometallic reagents and organic halides have changed the face of modern synthetic chemistry. However, the high reactivity and poor selectivity of common organolithium reagents have largely prohibited their use as a viable partner in direct catalytic cross-coupling. Here we report that in the presence of a Pd-phosphine catalyst, a wide range of alkyl-, aryl- and heteroaryl-lithium reagents undergo selective cross-coupling with aryl- and alkenyl-bromides. The process proceeds quickly under mild conditions (room temperature) and avoids the notorious lithium halogen exchange and homocoupling. The preparation of key alkyl-, aryl- and heterobiaryl intermediates reported here highlights the potential of these cross-coupling reactions for medicinal chemistry and material science.

Original languageEnglish
Pages (from-to)667-672
Number of pages6
JournalNature Chemistry
Volume5
Issue number8
DOIs
Publication statusPublished - Aug-2013

Keywords

  • GRIGNARD-REAGENTS
  • NOBEL LECTURE
  • C-C
  • PALLADIUM
  • HALIDES
  • ARYL
  • ELECTROPHILES
  • ARYLATION
  • ALKENYL

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