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Rhodium-Catalyzed Carbon-Silicon Bond Activation for Synthesis of Benzosilole Derivatives

Journal Of The American Chemical Society, 2012 Nov 28, Vol.134(47), pp.19477-19488 [Peer Reviewed Journal]

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  • Title:
    Rhodium-Catalyzed Carbon-Silicon Bond Activation for Synthesis of Benzosilole Derivatives
  • Author: Onoe, M ; Baba, K ; Kim, Y ; Kita, Y ; Tobisu, M ; Chatani, N
  • Found In: Journal Of The American Chemical Society, 2012 Nov 28, Vol.134(47), pp.19477-19488 [Peer Reviewed Journal]
  • Subjects: Carbon -- Chemistry ; Organometallic Compounds -- Chemistry ; Organosilicon Compounds -- Chemical Synthesis ; Rhodium -- Chemistry ; Silicon -- Chemistry
  • Language: English
  • Description: 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...
  • Identifier: ISSN: 0002-7863 ; DOI: 10.1021/ja3096174

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