AI Article Synopsis
- * This method allows for the effective nucleophilic addition and cyclization, leading to the di- and trifunctionalization of aryl sulfoxides, which are readily available.
- * The resulting dearomatization products can be transformed into a variety of complex structures, and the study provides insights into the mechanisms and selectivities of these reactions.
Article 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.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9372148 | PMC |
| http://dx.doi.org/10.1038/s41467-022-32426-6 | DOI Listing |
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