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Palladium‐Catalyzed Intermolecular Coupling of 2‐Silylaryl Bromides with Alkynes: Synthesis of Benzosiloles and Heteroarene‐Fused Siloles by Catalytic Cleavage of the C(sp 3 )Si Bond
Author(s) -
Liang Yun,
Geng Weizhi,
Wei Junnian,
Xi Zhenfeng
Publication year - 2012
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.201108154
Subject(s) - benzothiophene , chemistry , intermolecular force , catalysis , thiophene , palladium , bond cleavage , cleavage (geology) , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , molecule , materials science , fracture (geology) , composite material
Unusual split : A wide variety of benzosiloles and derivatives are obtained by the Pd‐catalyzed intermolecular coupling of 2‐silylaryl bromides and alkynes and the accompanying selective cleavage of the C(sp 3 )Si bonds as a key step (see scheme). The product spectrum includes benzosiloles, benzothiophene‐fused siloles, ladder‐type π‐conjugated benzosiloles, and thiophene‐bridged 2,5‐bisbenzosiloles.