4.8 Article

Neutral-Eosin-Y-Photocatalyzed Silane Chlorination Using Dichloromethane

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 36, Pages 12580-12584

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908556

Keywords

dichloromethane; hydrogen atom transfer; neutral eosin Y; Si-H activation; silyl chloride

Funding

  1. Ministry of Education (MOE) of Singapore [MOE2017-T2-2-081]
  2. GSK-EDB [R-143-000-687-592]
  3. National Natural Science Foundation of China [21702142, 21871205, 21425313]
  4. National University of Singapore (Suzhou) Research Institute

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Chlorosilanes are versatile reagents in organic synthesis and material science. A mild pathway is now reported for the quantitative conversion of hydrosilanes to silyl chlorides under visible-light irradiation using neutral eosin Y as a hydrogen-atom-transfer photocatalyst and dichloromethane as a chlorinating agent. Stepwise chlorination of di- and trihydrosilanes was achieved in a highly selective fashion assisted by continuous-flow micro-tubing reactors. The ability to access silyl radicals using photocatalytic Si-H activation promoted by eosin Y offers new perspectives for the synthesis of valuable silicon reagents in a convenient and green manner.

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