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Expedient Iron‐Catalyzed Coupling of Alkyl, Benzyl and Allyl Halides with Arylboronic Esters
Author(s) -
Bedford Robin B.,
Brenner Peter B.,
Carter Emma,
Carvell Thomas W.,
Cogswell Paul M.,
Gallagher Timothy,
Harvey Jeremy N.,
Murphy Damien M.,
Neeve Emily C.,
Nunn Joshua,
Pye Dominic R.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402174
Subject(s) - halide , alkyl , chemistry , reagent , phosphine , catalysis , adduct , combinatorial chemistry , organic chemistry , medicinal chemistry
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.