Sulfoxonium Ylides as Carbene Precursors in Rhodium-Catalyzed Sommelet-Hauser Rearrangement for the Synthesis of S/Se-Containing Compounds

被引：1
作者：
Luo, Cankun [1 ]
Lin, Zhiqian [1 ]
Hao, Yingdi [1 ]
Jia, Pengfei [1 ]
Lai, Ruizhi [1 ]
Guo, Li [1 ]
Yao, Yuan [2 ,3 ]
Wu, Yong [1 ]
机构：
[1] Sichuan Univ, Dept Med Chem, Chengdu 610041, Peoples R China
[2] Sichuan Univ, West China Sch Publ Hlth, Dept Geriatr & Cardiol, Chengdu 610041, Peoples R China
[3] Sichuan Univ, West China Hosp 4, Chengdu 610041, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 43期
关键词：
Carbene; Rearrangement; Rhodium; Sulfoxonium ylides; Sulfur; SELECTIVE SYNTHESIS; INSERTION REACTIONS; SELENONIUM YLIDE; SULFUR YLIDES; SELENIUM; DERIVATIVES; CHEMISTRY; BOND;
D O I：
10.1002/ejoc.202300690
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Rhodium-catalyzed Sommelet-Hauser rearrangement derived from & alpha;-thioesters/& alpha;-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 firstly 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 center. Sulfoxonium ylides as the safe carbene precursors are firstly used in Sommelet-Hauser rearrangement reactions for the synthesis of sulfur/selenium-containing compounds. The present reaction highlights the advantages of mild condition and broad substrate scope.image
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页数：5
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