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

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 construct...

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Published in:Nature communications 2022-08, Vol.13 (1), p.4719-4719, Article 4719
Main Authors: Hu, Mengjie, Liu, Yanping, Liang, Yuchen, Dong, Taotao, Kong, Lichun, Bao, Ming, Wang, Zhi-Xiang, Peng, Bo
Format: Article
Language:English
Subjects:
119/118
140/131
140/58
639/638/403/933
639/638/403/934
Aromatic compounds
Humanities and Social Sciences
Intermediates
Laboratories
multidisciplinary
Phenols
Science
Science (multidisciplinary)
Sulfoxides
Sulfur
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Summary: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. In contrast with well-established dearomatization protocols such as the Birch reduction, sigmatropic rearrangement-based dearomatizations are a less-explored but potentially effective route to saturated compounds. Here, the authors show a [5,5]-rearrangement-enabled dearomatization of aryl sulfoxides.
ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-022-32426-6