Visible-light-induced surfactant-promoted sulfonylation of alkenes and alkynes with sulfonyl chloride by the formation of an EDA-complex with NaI in water at room temperature

被引:60
|
作者
Lin, Li [1 ]
Yang, Zhonglie [1 ]
Liu, Jianchen [1 ]
Wang, Jingxia [2 ]
Zheng, Jiale [1 ]
Li, Jun-Long [3 ]
Zhang, Xiaobin [2 ]
Liu, Xiang-Wei [1 ]
Jiang, Hezhong [1 ]
Li, Jiahong [1 ]
机构
[1] Southwest Jiaotong Univ, Sch Life Sci & Engn, Sichuan Engn Res Ctr Biomimet Synth Nat Drugs, Chengdu 610031, Peoples R China
[2] Sichuan Inst Atom Energy, Irradiat Preservat Technol Key Lab Sichuan Prov, Chengdu 610101, Peoples R China
[3] Chengdu Univ, Sch Pharm, Sichuan Ind Inst Antibiot, Antibiot Res & Re Evaluat Key Lab Sichuan Prov, Chengdu 610106, Peoples R China
基金
中国国家自然科学基金;
关键词
ASYMMETRIC TRANSFER HYDROGENATION; TRANSITION-METAL-FREE; ARYLSULFONYL CHLORIDES; PHOTOREDOX; CATALYST; CYCLIZATION; KETOESTERS; REDUCTION; ARYLATION;
D O I
10.1039/d1gc00956g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A green and efficient visible-light-induced iodosulfonyl reaction of alkenes in water using an EDA complex strategy at room temperature has been disclosed. The addition of a cationic surfactant allows for the easy formation of colored EDA complexes in water. The hydrophobic effect of the core in the surfactant aggregates, which act as a reaction medium formed by the surfactants themselves in water, plays a significant role in stabilizing the transition state and decreasing the activation energy of the reaction. Remarkably, transition-metal catalysts and organic solvents were not required in this transformation. Moreover, it displayed a broad substrate scope, good functional group tolerance, simple operation, scalability and high chemical selectivity. Thus, it not only provided a green and efficient synthetic strategy for the preparation of beta-iodo-substituted sulfone derivatives, but also enriched the investigation of visible-light-induced reactions in water.
引用
收藏
页码:5467 / 5473
页数:7
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