Expedient Iron‐Catalyzed Coupling of Alkyl,Benzyl and Allyl Halides with Arylboronic Esters |
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| Authors: | Prof. Dr. Robin B. Bedford Dr. Peter B. Brenner Dr. Emma Carter Thomas W. Carvell Paul M. Cogswell Prof. Dr. Timothy Gallagher Prof. Dr. Jeremy N. Harvey Prof. Dr. Damien M. Murphy Dr. Emily C. Neeve Joshua Nunn Dominic R. Pye |
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| Affiliation: | 1. School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS (UK);2. School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT (UK) |
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| 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. |
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| Keywords: | alkyl halides catalysis cross‐coupling iron Suzuki coupling |
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