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Issue 2, 2015
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Cobalt co-catalysis for cross-electrophile coupling: diarylmethanes from benzyl mesylates and aryl halides

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Abstract

The nickel-catalyzed cross-coupling of aryl halides with alkyl radicals derived from alkyl halides has recently been extended to couplings with carbon radicals generated by a co-catalyst. In this study, a new co-catalyst, cobalt phthalocyanine (Co(Pc)), is introduced and demonstrated to be effective for coupling substrates not prone to homolysis. This is because Co(Pc) reacts with electrophiles by an SN2 mechanism instead of by the electron-transfer or halogen abstraction mechanisms previously explored. Studies demonstrating the orthogonal reactivity of (bpy)Ni and Co(Pc), applying this selectivity to the coupling of benzyl mesylates with aryl halides, and the adaptation of these conditions to the less reactive benzyl phosphate ester and an enantioconvergent reaction are presented.

Graphical abstract: Cobalt co-catalysis for cross-electrophile coupling: diarylmethanes from benzyl mesylates and aryl halides

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The article was received on 09 Oct 2014, accepted on 07 Nov 2014 and first published on 10 Nov 2014


Article type: Edge Article
DOI: 10.1039/C4SC03106G
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Citation: Chem. Sci., 2015,6, 1115-1119
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    Cobalt co-catalysis for cross-electrophile coupling: diarylmethanes from benzyl mesylates and aryl halides

    L. K. G. Ackerman, L. L. Anka-Lufford, M. Naodovic and D. J. Weix, Chem. Sci., 2015, 6, 1115
    DOI: 10.1039/C4SC03106G

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