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Me3SiSiMe2(OnBu): a disilane reagent for the synthesis of diverse silacycles via Brook- and retro-Brook-type rearrangement† † Electronic supplementary information (ESI) available. CCDC 2040657–2040659. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/d1sc03487a

ABSTRACT: Herein, a readily available disilane Me3SiSiMe2(OnBu) 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. A readily available disilane Me3SiSiMe2(OnBu) as a silylene source has been developed for the synthesis of diverse silacycles via Brook- and retro-Brook-type rearrangement.

SUBMITTER: Xu Y

PROVIDER: S-EPMC8442712 | biostudies-literature |

REPOSITORIES: biostudies-literature

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