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Photo-Induced Thiolate Catalytic Activation of Inert Caryl-Hetero Bonds for Radical Borylation

preprint
submitted on 29.11.2020, 08:29 and posted on 01.12.2020, 08:00 by Shun Wang, Hua Wang, Burkhard Koenig
Cross-coupling reactions are essential tools in modern synthesis of drugs, natural products and materials. The recent developments in photocatalytic radical generation have improved and expanded the classic metal-catalyzed cross coupling reactions even further. However, for sp2 cross coupling reactions aryl halides or related active leaving groups, such as triflates, are required. Substituted arenes bearing strong C-X bonds remain inert to current methods. We describe now a new thiolate photocatalysis for the activation of inert substituted arenes in ipso-borylation reactions. This catalytic system exhibits strong reducing power and allows the borylation of stable Caryl−F, Caryl−O, Caryl-N and Caryl−S bonds, which are considered as chemically stable at mild reaction conditions. Our method considerably widens the available substrate scope of aryl radical precursors and we anticipate that this report will inspire new chemistry based on inert chemical bond activation.

Funding

European Research Council (ERC) under the European Unions Horizon 2020 research and innovation programme (grant agreement No. 741623)

China Scholarship Council (CSC) for a predoctoral fellowship (CSC student number 201606280052)

History

Email Address of Submitting Author

burkhard.koenig@chemie.uni-regensburg.de

Institution

University of Regensburg

Country

Germany

ORCID For Submitting Author

0000-0002-6131-4850

Declaration of Conflict of Interest

No conflicts of interest

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