1160757-33-4Relevant academic research and scientific papers
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
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.
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.
