Tian, Ya-Ming and Pu, Xiang and Sanchez, Alejandro Heredero and Silva, Wagner and Gschwind, Ruth M. and Koenig, Burkhard (2025) Photoinduced Radical Borylation of Robust Carbon-Heteroatom Bonds. ADVANCED SYNTHESIS & CATALYSIS, 367 (2). ISSN 1615-4150, 1615-4169
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Photoinduced borylation has emerged as a valuable strategy for synthesizing arylboronic esters. However, photochemical transformations involving inert bonds such as C(sp2)-F bonds are still challenging. Herein, we report a straightforward and operationally simple method for the activation of various inert carbon-heteroatom bonds, enabling the synthesis of diverse arylboronic esters without the need for transition metals or catalysts. Mechanistic investigations reveal that the deprotonation of DMSO plays a pivotal role in the reaction, and the excited DMSO anion can undergo electron transfer to the aryl substrates activated by anionic sp2-sp3 diboron compounds, i. e., [FB2pin2]-, thereby facilitating the cleavage of carbon-heteroatom bonds. The reaction allows the conversion of diverse Caryl-hetero bonds in batch and flow reactors into the corresponding arylboronic esters. The products can be used in a subsequent Suzuki-Miyaura cross-coupling without isolation.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | METAL-FREE BORYLATION; CATALYZED BORYLATION; ARYL HALIDES; BUILDING-BLOCKS; BORON; POLYFLUOROARENES; ACTIVATION; VERSATILE; POLYMERS; BROMIDES; Borylation; Photochemistry; Inert carbon-heteroatom bonds; DMSO anion; Transition-metal-free |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Ruth Gschwind |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 17 Mar 2026 06:46 |
| Last Modified: | 17 Mar 2026 06:46 |
| URI: | https://pred.uni-regensburg.de/id/eprint/64251 |
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