1160757-38-9Relevant academic research and scientific papers
Palladium-catalyzed intermolecular coupling of 2-silylaryl bromides with alkynes: Synthesis of benzosiloles and heteroarene-fused siloles by catalytic cleavage of the C(sp3)-Si bond
Liang, Yun,Geng, Weizhi,Wei, Junnian,Xi, Zhenfeng
, p. 1934 - 1937 (2012/03/26)
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(sp3)-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.
Rhodium-catalyzed carbon-silicon bond activation for synthesis of benzosilole derivatives
Onoe, Masahiro,Baba, Katsuaki,Kim, Yoonjoo,Kita, Yusuke,Tobisu, Mamoru,Chatani, Naoto
supporting information, p. 19477 - 19488 (2013/02/21)
A rhodium-catalyzed coupling reaction of 2-trimethylsilylphenylboronic acid with internal alkynes is developed for the synthesis of 2,3-disubstituted benzosilole derivatives. A range of functional groups, encompassing ketones, esters, amines, aryl bromides, and heteroarenes, are compatible, which provides rapid access to diverse benzosiloles. Sequential 2-fold coupling enables modular synthesis of asymmetrically substituted 1,5-dihydro-1,5-disila-s-indacene, a π-extended molecule of interest in organic electronics. In terms of the mechanism, the reaction involves cleavage of a C(alkyl)-Si bond in a trialkylsilyl group, which normally requires extremely harsh conditions for activation. Mechanistic studies, including effects of substituents, reveal that C-Si bond cleavage does not proceed through a hypercoordinated silicon species, but rather through a rhodium-mediated activation process. The potential use of the reaction in catalytic asymmetric synthesis of Si-chiral benzosiloles is also demonstrated.
Iron-catalyzed aryl- and alkenyllithiation of alkynes and its application to benzosilole synthesis
Shirakawa, Eiji,Masui, Seiji,Narui, Rintaro,Watabe, Ryo,Ikeda, Daiji,Hayashi, Tamio
supporting information; experimental part, p. 9714 - 9716 (2011/10/02)
Phenyl- and vinyllithiums having an alkyl substituent at their ortho- and cis-position, respectively, readily added to alkynes in the presence of 5 mol% of Fe(acac)3. The reaction of o-(trimethylsilyl)phenyllithium with alkynes gave benzosilole
Rhodium-catalyzed coupling of 2-silylphenylboronic acids with alkynes leading to benzosiloles: Catalytic cleavage of the carbon-silicon bond in trialkylsilyl groups
Tobisu, Mamoru,Onoe, Masahiro,Kita, Yusuke,Chatani, Naoto
scheme or table, p. 7506 - 7507 (2009/10/17)
(Chemical Equation Presented) The reaction of 2-(trimethylsilyl) phenylboronic acid with alkynes in the presence of a rhodium catalyst affords benzosilole derivatives. The arylvinylrhodium intermediate undergoes formal substitution at a silicon center, resulting in the cleavage of a robust silicon-methyl bond in the trimethylsilyl group.
