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Published on: February 24, 2015
Visible-light-induced radical reaction of acylsilanes through solvent-controlled Norrish type I cleavage
Nuo-Yan Li1, Wang Zhang1, Dan-Ni Yang1
1Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; Anhui Provincial Key Laboratory of Synthetic Chemistry and Applications; College of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000, People's Republic of China. hanmy10@126.com.
None:
The development of innovative photoinduced reactions for acylsilanes remains a significant challenge in organic synthesis, primarily due to their inherent propensity to undergo 1,2-Brook rearrangement upon photoirradiation, generating siloxycarbene intermediates. In this study, we demonstrate that the reactivity of acylsilanes under visible light can be regulated to effectively suppress the undesirable 1,2-Brook rearrangement. This control is achieved by employing polar solvents as the reaction medium during photoirradiation, strategically redirecting the reaction pathway toward Norrish type I cleavage. As a result, acylsilanes afford acyl radicals and silyl radicals, which enables the selective capture of acyl radicals by diselenides for the chemoselective synthesis of a diverse array of selenoester products.
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