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Gold(I) carbenes by retro-Buchner reaction: generation and fate.


ABSTRACT: The fate of the aryl gold(I) carbenes generated by retro-Buchner reaction of ortho-substituted 7-aryl-1,3,5-cycloheptatrienes is dependent on the constitution of the ortho substituent. Indenes and fluorenes are obtained by intramolecular reaction of highly electrophilic gold(I) carbenes with alkenes and arenes. According to density functional theory calculations, the gold-catalyzed retro-Buchner process occurs stepwise, although the two carbon-carbon cleavages occur on a rather flat potential energy surface.

SUBMITTER: Wang Y 

PROVIDER: S-EPMC3898715 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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Gold(I) carbenes by retro-Buchner reaction: generation and fate.

Wang Yahui Y   McGonigal Paul R PR   Herlé Bart B   Besora Maria M   Echavarren Antonio M AM  

Journal of the American Chemical Society 20131231 2


The fate of the aryl gold(I) carbenes generated by retro-Buchner reaction of ortho-substituted 7-aryl-1,3,5-cycloheptatrienes is dependent on the constitution of the ortho substituent. Indenes and fluorenes are obtained by intramolecular reaction of highly electrophilic gold(I) carbenes with alkenes and arenes. According to density functional theory calculations, the gold-catalyzed retro-Buchner process occurs stepwise, although the two carbon-carbon cleavages occur on a rather flat potential en  ...[more]

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