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Dearomative di- and trifunctionalization of aryl sulfoxides via [5,5]-rearrangement.

ABSTRACT: Aromatic [5,5]-rearrangement can in principle be an ideal protocol to access dearomative compounds. However, the lack of competent [5,5]-rearrangement impedes the advance of the protocol. In this Article, we showcase the power of [5,5]-rearrangement recently developed in our laboratory for constructing an intriguing dearomative sulfonium specie which features versatile and unique reactivities to perform nucleophilic 1,2- and 1,4-addition and cyclization, thus achieving dearomative di- and trifunctionalization of easily accessible aryl sulfoxides. Impressively, the dearomatization products can be readily converted to sulfur-removed cyclohexenones, naphthalenones, bicyclic cyclohexadienones, and multi-substituted benzenes. Mechanistic studies shed light on the key intermediates and the remarkable chemo-, regio- and stereoselectivities of the reactions.

SUBMITTER: Hu M

PROVIDER: S-EPMC9372148 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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Dearomative di- and trifunctionalization of aryl sulfoxides via [5,5]-rearrangement.

Hu Mengjie M Liu Yanping Y Liang Yuchen Y Dong Taotao T Kong Lichun L Bao Ming M Wang Zhi-Xiang ZX Peng Bo B

Nature communications 20220811 1

Aromatic [5,5]-rearrangement can in principle be an ideal protocol to access dearomative compounds. However, the lack of competent [5,5]-rearrangement impedes the advance of the protocol. In this Article, we showcase the power of [5,5]-rearrangement recently developed in our laboratory for constructing an intriguing dearomative sulfonium specie which features versatile and unique reactivities to perform nucleophilic 1,2- and 1,4-addition and cyclization, thus achieving dearomative di- and trifun ...[more]

PMID: 35953490

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