1016642-73-1Relevant academic research and scientific papers
A multi-substituted silacyclopentadiene derivative synthesis method
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Paragraph 0030-0032, (2017/03/08)
The invention provides a synthesis method of a polysubstituted silole derivative. The polysubstituted silole derivative is prepared by reacting a 2-(trimethylsilyl)aryl trifluoromethane sulfonate derivative with alkyne in the presence of a catalyst. The synthesis method is pretty high in yield rate, scientific, reasonable, accessible in raw materials, wide in application range, high in separation yield rate, simple in experiment equipment, simple and easy in operation implementation, and conductive to further development and application.
Palladium-catalyzed cleavage of the Me-Si bond in ortho-trimethylsilyl aryltriflates: Synthesis of benzosilole derivatives from ortho-trimethylsilyl aryltriflates and alkynes
Meng, Tianhao,Ouyang, Kunbing,Xi, Zhenfeng
, p. 14273 - 14276 (2013/09/02)
An efficient Pd-catalyzed cleavage of the Me-Si bond in ortho-trimethylsilyl aryltriflates was realized and synthetically applied. Most of the commercially available ortho-trimethylsilyl aryltriflates could undergo the Pd-catalyzed intermolecular coupling with alkynes via cleavage of the Me-Si bond, which represents a new reaction pattern of ortho-trimethylsilyl aryltriflates. Potassium bromide (KBr) was found effective for this process. A variety of benzosilole derivatives were thus generated in high yields. The Royal Society of Chemistry 2013.
Rhodium-catalyzed carbon-silicon bond activation for synthesis of benzosilole derivatives
Onoe, Masahiro,Baba, Katsuaki,Kim, Yoonjoo,Kita, Yusuke,Tobisu, Mamoru,Chatani, Naoto
, 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.
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.
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
supporting information; experimental part, 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.
Modular synthesis of functionalized benzosiloles by tin-mediated cyclization of (o-alkynylphenyl)silane
Ilies, Laurean,Tsuji, Hayato,Sato, Yoshiharu,Nakamura, Eiichi
, p. 4240 - 4241 (2008/09/21)
Trimethylstannyllithium promotes cyclization of (o-alkynylphenyl)silane into a 3-stannylbenzosilole, via addition to the triple bond followed by intramolecular cyclization in a cascade fashion. This intermediate can be functionalized with either electrophiles or nucleophiles to allow modular synthesis of 2,3-disubstituted benzosiloles. One of these compounds, a phenylene-bis(benzosilole) compound, shows electron drift mobility as high as 6 × 10-4 cm2/Vs in an amorphous film, making this class of compounds promising electronic materials for organic light emitting devices and organic photovoltaic cells. Copyright
