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Issue 74, 2016
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The copper-catalysed Suzuki–Miyaura coupling of alkylboron reagents: disproportionation of anionic (alkyl)(alkoxy)borates to anionic dialkylborates prior to transmetalation

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Abstract

We report the first example of CuI-catalysed coupling of alkylboron reagents with aryl and heteroaryl iodides that affords products in good to excellent yields. Preliminary mechanistic studies with alkylborates indicate that the anionic (alkoxy)(alkyl)borates, generated from alkyllithium and alkoxyboron reagents, undergo disproportionation to anionic dialkylborates and that both anionic alkylborates are active for transmetalation to a CuI-catalyst. Results from a radical clock experiment and the Hammett plot imply that the reaction likely proceeds via a non-radical pathway.

Graphical abstract: The copper-catalysed Suzuki–Miyaura coupling of alkylboron reagents: disproportionation of anionic (alkyl)(alkoxy)borates to anionic dialkylborates prior to transmetalation

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Publication details

The article was received on 21 Jun 2016, accepted on 11 Aug 2016 and first published on 11 Aug 2016


Article type: Communication
DOI: 10.1039/C6CC05114F
Citation: Chem. Commun., 2016,52, 11072-11075
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    The copper-catalysed Suzuki–Miyaura coupling of alkylboron reagents: disproportionation of anionic (alkyl)(alkoxy)borates to anionic dialkylborates prior to transmetalation

    P. Basnet, S. Thapa, D. A. Dickie and R. Giri, Chem. Commun., 2016, 52, 11072
    DOI: 10.1039/C6CC05114F

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