Gold(I) Carbenes by Retro-Buchner Reaction: Generation and Fate | Zendy

Yahui Wang | Zendy; Paul R. McGonigal | Zendy; Bart Herlé | Zendy; María Besora | Zendy; Antonio M. Echavarren | Zendy

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Gold(I) Carbenes by Retro-Buchner Reaction: Generation and Fate

Author(s) -

Yahui Wang,

Paul R. McGonigal,

Bart Herlé,

María Besora,

Antonio M. Echavarren

Publication year - 2013

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja411626v

Subject(s) - chemistry , substituent , intramolecular force , electrophile , aryl , density functional theory , photochemistry , computational chemistry , carbene , catalysis , medicinal chemistry , stereochemistry , organic chemistry , alkyl

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.

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