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

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 and Pye, Dominic R. 2014. Expedient iron-catalyzed coupling of alkyl, benzyl and allyl halides with aylboronic esters. Chemistry - a European Journal 20 (26) , pp. 7935-7938. 10.1002/chem.201402174

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: alkyl halides; catalysis; cross-coupling; iron; Suzuki coupling
Publisher: Wiley Blackwell
ISSN: 0947-6539
Funders: EPSRC
Last Modified: 17 Jun 2019 02:45

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