Me₃SiSiMe₂(O ⁿ Bu): a disilane reagent for the synthesis of diverse silacycles via Brook- and retro-Brook-type rearrangement.

ABSTRACT: Herein, a readily available disilane Me₃SiSiMe₂(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)-1H-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.

SUBMITTER: Xu Y 

PROVIDER: S-EPMC8442712 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature