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

Mengjie Hu, Yanping Liu, Yuchen Liang, Taotao Dong, Lichun Kong, Ming Bao, Zhi-Xiang Wang () and Bo Peng ()
Additional contact information
Mengjie Hu: Zhejiang Normal University
Yanping Liu: Zhejiang Normal University
Yuchen Liang: Zhejiang Normal University
Taotao Dong: Zhejiang Normal University
Lichun Kong: Zhejiang Normal University
Ming Bao: Dalian University of Technology
Zhi-Xiang Wang: University of the Chinese Academy of Sciences
Bo Peng: Zhejiang Normal University

Nature Communications, 2022, vol. 13, issue 1, 1-11

Abstract: 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.

Date: 2022
References: View references in EconPapers View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-022-32426-6 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-32426-6

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-022-32426-6

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().