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Issue 23, 2019
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Sterically controlled C–H/C–H homocoupling of arenes via C–H borylation

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Abstract

A mild one-pot protocol for the synthesis of symmetrical biaryls by sequential Ir-catalyzed C–H borylation and Cu-catalyzed homocoupling of arenes is described. The regiochemistry of the biaryl formed is sterically controlled as dictated by the C–H borylation step. The methodology is also successfully extended to heteroarenes. Some of the products obtained by this approach are impossible to obtain via the Ullmann or the Suzuki coupling protocols. Finally, we have shown a one-pot sequence describing C–H borylation/Cu-catalyzed homocoupling/Pd-catalyzed Suzuki coupling to obtain π-extended arene frameworks.

Graphical abstract: Sterically controlled C–H/C–H homocoupling of arenes via C–H borylation

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Publication details

The article was received on 30 Apr 2019, accepted on 20 May 2019 and first published on 21 May 2019


Article type: Communication
DOI: 10.1039/C9OB00995G
Org. Biomol. Chem., 2019,17, 5703-5707

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    Sterically controlled C–H/C–H homocoupling of arenes via C–H borylation

    X. Pei, G. Zhou, X. Li, Y. Xu, R. C. Panicker and R. Srinivasan, Org. Biomol. Chem., 2019, 17, 5703
    DOI: 10.1039/C9OB00995G

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