Neutral‐Eosin‐Y‐Photocatalyzed Silane Chlorination Using Dichloromethane

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 c...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-09, Vol.58 (36), p.12580-12584
Main Authors: Fan, Xuanzi, Xiao, Pin, Jiao, Zeqing, Yang, Tingting, Dai, Xiaojuan, Xu, Wengang, Tan, Jin Da, Cui, Ganglong, Su, Hongmei, Fang, Weihai, Wu, Jie
Format: Article
Language:English
Subjects:
Chlorination
Chlorosilanes
Dichloromethane
hydrogen atom transfer
Irradiation
Light irradiation
neutral eosin Y
Photocatalysis
Radiation
Reagents
Silicon
silyl chloride
Si−H activation
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Summary: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. A mild and convenient silane chlorination has been achieved using neutral eosin Y as a direct hydrogen‐atom‐transfer photocatalyst and dichloromethane as both the solvent and the chlorinating reagent. Selective stepwise chlorination of di‐ and trihydrosilanes was achieved in a controllable manner using continuous‐flow micro‐tubing reactors.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201908556