DOI: 10.1002/ejoc.202300690 ISSN:
Sulfoxonium Ylides as Carbene Precusors in Rhodium‐Catalyzed Sommelet‐Hauser Rearrangement for the Synthesis of S/Se‐Containing Compounds
Cankun Luo, Zhiqian Lin, Yingdi Hao, Pengfei Jia, Ruizhi Lai, Li Guo, Yuan Yao, Yong Wu- Organic Chemistry
- Physical and Theoretical Chemistry
Rhodium‐catalyzed Sommelet‐Hauser rearrangement derived from α‐thioesters/α‐selenoesters and sulfoxonium ylides has been developed for the synthesis of various sulfur/selenium‐containing ortho‐substituted aromatic compounds in medium to excellent yields (39 examples; up to 97%). Sulfoxonium ylides as the safe carbene precursors are first used in Sommelet‐Hauser rearrangement reactions, which is superior to traditional diazo compounds. The present reaction has the advantages of mild condition, safety and broad substrate scope, which afford a unique method for the synthesis of sulfur/selenium‐containing compounds with a tertiary carbon centre.