期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 26, 期 24, 页码 5360-5364出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202000603
关键词
decarboxylation; gem-bisboronates; organoborones; photochemistry; radicals
资金
- Azrieli Foundation
- Hebrew University
The use of gem-diborylalkenes as radical-reactive groups is explored for the first time. These reactions provide an efficient and general method for the photochemical conversion of gem-diborylalkenes to rapidly access 1,1-bisborylalkanes. This method exploits a novel photoredox decarboxylative radical addition to gem-diborylalkenes to afford alpha-gem-diboryl carbon-centered radicals, which benefit from additional stability by virtue of an interaction with the empty p-orbitals on borons. The reaction offers a highly modular and regioselective approach to gamma-amino gem-diborylalkanes. Furthermore, EPR spectroscopy and DFT calculations have provided insight into the radical mechanism underlying the photochemistry reaction and the stability of the bis-metalated radicals, respectively.
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