Solvent-free aromatic C–H functionalisation/halogenation reactions

Robin B. Bedford, Jens U. Engelhart, Mairi F. Haddow, Charlotte J. Mitchell, Ruth L. Webster

Research output: Contribution to journalArticlepeer-review

42 Citations (Scopus)

Abstract

The solvent-free, palladium-catalysed reaction of anilides with CuCl2 in the presence or absence of copper acetate yields ortho-chlorinated anilides in good to excellent yields, even on a large scale (100 mmol). By contrast, the equivalent reactions with copper bromide, either solvent free or in 1,2-dichloroethane, in the presence or absence of palladium, under air or inert conditions, gave the products of simple electrophilic bromination. Mechanistic studies highlighted the involvement of palladacyclic intermediates, one of which was characterised crystallographically, which undergo subsequent reaction with copper(II) chloride to yield the chlorinated anilide products.
Original languageEnglish
Pages (from-to)10464-10472
JournalDalton Transactions
Volume39
Issue number43
Early online date7 Oct 2010
DOIs
Publication statusPublished - 2010

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