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

descriptionPublicationkeyboard_double_arrow_right Article 31 Dec 2013 English Publisher:American Chemical Society (ACS)Journal:Journal of the American Chemical Society, volume 136, pages 801-809 (issn: 0002-7863, eissn: 1520-5126,

Copyright policy )Funded by:EC | CATGOLD, EC | ATMOL

Authors: Yahui Wang; Paul R. McGonigal; Bart Herlé; Maria Besora; Antonio M. Echavarren;

doi: 10.1021/ja411626v

pmid: 24358986

pmc: PMC3898715

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

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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.

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