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Issue 91, 2018
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Alkylarylation of styrenes via direct C(sp3)–Br/C(sp2)–H functionalization mediated by photoredox and copper cooperative catalysis

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Abstract

For straightforward access to various substituted 1,1-diarylalkanes a photoredox-catalyzed and copper-promoted 1,2-alkylarylation reaction of styrenes has been developed, which uses α-carbonyl alkyl bromides and N,N-disubstituted anilines as functionalization reagents. In this radical difunctionalization reaction, α-carbonyl alkyl bromides, including primary-, secondary- and tertiary-α-bromoalkyl ketone esters, malonic esters and cycloalkane were transformed to the corresponding 1,1-diarylalkanes in moderate to good yields at room temperature. Notably, this transformation provided a new route for the C–H alkylation of N,N-disubstituted anilines with high para-selectivity beyond the typical Friedel–Crafts alkylation.

Graphical abstract: Alkylarylation of styrenes via direct C(sp3)–Br/C(sp2)–H functionalization mediated by photoredox and copper cooperative catalysis

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Publication details

The article was received on 19 Sep 2018, accepted on 17 Oct 2018 and first published on 17 Oct 2018


Article type: Communication
DOI: 10.1039/C8CC07587E
Citation: Chem. Commun., 2018,54, 12816-12819

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    Alkylarylation of styrenes via direct C(sp3)–Br/C(sp2)–H functionalization mediated by photoredox and copper cooperative catalysis

    X. Yong, Y. Han, Y. Li, R. Song and J. Li, Chem. Commun., 2018, 54, 12816
    DOI: 10.1039/C8CC07587E

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