Expedient iron-catalyzed coupling of alkyl, benzyl and allyl halides with arylboronic esters

Robin B Bedford, Peter B Brenner, Emma Carter, Tom W Carvell, Paul M Cogswell, Tim C Gallagher, Jeremy N Harvey, Damien M Murphy, Emily C Neeve, Joshua Nunn, Dominic R Pye

Research output: Contribution to journalArticle (Academic Journal)peer-review

70 Citations (Scopus)

Abstract

While attractive, the iron-catalyzed coupling of arylboron reagents with alkyl halides typically requires expensive or synthetically challenging diphosphine ligands. Herein, we show that primary and secondary alkyl bromides and chlorides, as well as benzyl and allyl halides, can be coupled with arylboronic esters, activated with alkyllithium reagents, by using very simple iron-based catalysts. The catalysts used were either adducts of inexpensive and widely available diphosphines or, in a large number of cases, simply [Fe(acac)3 ] with no added co- ligands. In the former case, preliminary mechanistic studies highlight the likely involvement of iron(I)-phosphine intermediates.

Original languageEnglish
Pages (from-to)7935-7938
Number of pages4
JournalChemistry - A European Journal
Volume20
Issue number26
DOIs
Publication statusPublished - 23 Jun 2014

Bibliographical note

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Structured keywords

  • BCS and TECS CDTs

Keywords

  • alkyl halides
  • catalysis
  • cross-coupling
  • iron
  • Suzuki coupling
  • GRIGNARD-REAGENTS
  • ALKENYL HALIDES

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