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

01 December 2020, Version 1
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.


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.


borylation reaction
Thiolate photocatalyst
EDA complex-promoted reaction
carbon fluorine bond activation
carbon oxygen bond activation
carbon sulfur bond activation
carbon nitrogen bond activation

Supplementary materials

Supporting Information -Shun Wang


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