Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 26, Pages 10639-10644Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202003070
Keywords
decarboxylation; deuteration; germyl radicals; photocatalysis; silyl radicals
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Funding
- JSPS [17H05430, 17H06173, 18K06544]
- JST CREST Program [JPMJCR19R2]
- Grants-in-Aid for Scientific Research [17H06173, 18K06544] Funding Source: KAKEN
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Silicon-containing compounds are widely used as synthetic building blocks, functional materials, and bioactive reagents. In particular, silyl radicals are important intermediates for the synthesis and transformation of organosilicon compounds. Herein, we describe the first protocol for the generation of silyl radicals by photoinduced decarboxylation of silacarboxylic acids, which can be easily prepared in high yield on a gram scale and are very stable to air and moisture. Irradiation of silacarboxylic acids with blue LEDs (455 nm) in the presence of a commercially available photocatalyst releases silyl radicals, which can further react with various alkenes to give the corresponding silylated products in good-to-high yields with broad functional-group compatibility. This reaction proceeds in the presence of water, enabling efficient deuterosilylation of alkenes with D2O as the deuterium source. Germyl radicals were similarly obtained.
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