Me 3 SiSiMe 2 (O n Bu): a disilane reagent for the synthesis of diverse silacycles via Brook- and retro-Brook-type rearrangement

Herein, a readily available disilane Me 3 SiSiMe 2 (O n Bu) has been developed for the synthesis of diverse silacycles via Brook- and retro-Brook-type rearrangement. This protocol enables the incorporation of a silylene into different starting materials, including acrylamides, alkene-tethered 2-(2-i...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2021-09, Vol.12 (35), p.11756-11761
Main Authors: Xu, Yankun, Xu, Weiwei, Chen, Xinyang, Luo, Xiai, Lu, Haiyan, Zhang, Minghao, Yang, Xiumei, Deng, Guobo, Liang, Yun, Yang, Yuan
Format: Article
Language:English
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Summary:Herein, a readily available disilane Me 3 SiSiMe 2 (O n Bu) has been developed for the synthesis of diverse silacycles via Brook- and retro-Brook-type rearrangement. This protocol enables the incorporation of a silylene into different starting materials, including acrylamides, alkene-tethered 2-(2-iodophenyl)-1 H -indoles, and 2-iodobiaryls, via the cleavage of Si–Si, Si–C, and Si–O bonds, leading to the formation of spirobenzosiloles, fused benzosiloles, and π-conjugated dibenzosiloles in moderate to good yields. Preliminary mechanistic studies indicate that this transformation is realized by successive palladium-catalyzed bis-silylation and Brook- and retro-Brook-type rearrangement of silane-tethered silanols.
ISSN:2041-6520
2041-6539
DOI:10.1039/D1SC03487A