Effect of Ring Sizes of Cyclooligosilanes on Construction of Organosilicon Clusters

Kyushin, Soichiro; Ishida, Shintaro; Tsurusaki, Akihiro; Otsuka, Kyohei

doi:10.5059/yukigoseikyokaishi.72.1290

Cited by 6 publications

References 87 publications

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Copper‐Catalyzed Ring‐Opening Silylation of Benzofurans with Disilane

2018

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The catalytic ring-opening silylation of benzofurans has been achieved by employingac opper catalyst and 1,2-ditert-butoxy-1,1,2,2-tetramethyldisilane,w hichc ould be easily prepared and handled without special care.T he reaction afforded (E)-o-(b-silylvinyl)phenols with complete stereoselectivity.T he scope of benzofurans was well explored, and functional groups such as chloro,f luoro,a nd acetal were compatible with the reaction conditions.D FT calculations were used to determine the energy profile of the silylation and the origin of the stereoselectivity.T he silylated product was proven to be useful as as ynthetic intermediate and subsequently underwent transformations such as Pd-catalyzed crosscoupling with iodoarenes.

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Copper‐Catalyzed Ring‐Opening Silylation of Benzofurans with Disilane

2018

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show abstract

Copper‐Catalyzed Ring‐Opening Silylation of Benzofurans with Disilane

2018

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The catalytic ring-opening silylation of benzofurans has been achieved by employing a copper catalyst and 1,2-di-tert-butoxy-1,1,2,2-tetramethyldisilane, which could be easily prepared and handled without special care. The reaction afforded (E)-o-(β-silylvinyl)phenols with complete stereoselectivity. The scope of benzofurans was well explored, and functional groups such as chloro, fluoro, and acetal were compatible with the reaction conditions. DFT calculations were used to determine the energy profile of the silylation and the origin of the stereoselectivity. The silylated product was proven to be useful as a synthetic intermediate and subsequently underwent transformations such as Pd-catalyzed cross-coupling with iodoarenes.

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