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Copper‐Catalyzed Ring‐Opening Silylation of Benzofurans with Disilane
Author(s) -
Saito Hayate,
Nogi Keisuke,
Yorimitsu Hideki
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201806237
Subject(s) - silylation , disilane , stereoselectivity , chemistry , catalysis , ring (chemistry) , acetal , copper , organic chemistry , phenols , medicinal chemistry , silane
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.