Synthesis of γ-keto sulfones through sulfonylation/acylation of alkenes merging NHC- and photo-catalysis

被引：1
作者：
Sun, Xu [1 ,2 ]
Zhang, Gan [1 ,2 ]
Ye, Bo [4 ]
Yang, Wen-Chao [5 ,6 ]
Wang, Lei [1 ,2 ,3 ]
Xie, Xiaoyu [1 ,2 ]
Zhang, Yicheng [1 ,2 ]
Liu, Jie [1 ,2 ]
机构：
[1] Huaibei Normal Univ, Key Lab Green & Precise Synthet Chem, Minist Educ, Huaibei 235000, Anhui, Peoples R China
[2] Huaibei Normal Univ, Dept Chem & Mat Sci, Huaibei 235000, Anhui, Peoples R China
[3] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Key Lab Organosilicon Chem & Mat Technol, Minist Educ, Hangzhou 311121, Zhejiang, Peoples R China
[4] Ecol & Environm Dept Linhai, Taizhou 317000, Zhejiang, Peoples R China
[5] Yangzhou Univ, Guangling Coll, Yangzhou 225009, Peoples R China
[6] Yangzhou Univ, Sch Plant Protect, Yangzhou 225009, Peoples R China
来源：
MOLECULAR CATALYSIS | 2024年 / 569卷
基金：
中国国家自然科学基金;
关键词：
gamma-keto sulfones; Alkenes; Sodium sulfinates; Acyl imidazoles; ANTIBACTERIAL;
D O I：
10.1016/j.mcat.2024.114563
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A three-component coupling of alkenes, sodium sulfinates and acyl imidazoles to access gamma-keto sulfones with good functional group tolerance via cooperative N-heterocyclic carbene (NHC)/photocatalysis is developed. Radical mechanism was proposed for the cascade reaction, revealing that a rare radical/radical cation cross- coupling reaction plays an important role.
引用
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页数：9
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共 71 条
[1]   Sulfones: new reagents in organocatalysis [J].
Alba, Andrea-Nekane R. ;
Companyo, Xavier ;
Rios, Ramon .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2018-2033
[2]   Visible-Light-Induced Radical Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CF2H-Substituted Quinazolinones [J].
Chen, Xiaoyu ;
Liu, Bo ;
Pei, Congcong ;
Li, Jingya ;
Zou, Dapeng ;
Wu, Yangjie ;
Wu, Yusheng .
ORGANIC LETTERS, 2021, 23 (20) :7787-7791
[3]   Photoredox-promoted co-production of 3,4-dihydroisoquinoline and H2 over Pd-doped leaf-like CdS catalyst [J].
Chen, Yu ;
Qi, Ming-Yu ;
Tang, Zi-Rong .
MOLECULAR CATALYSIS, 2024, 561
[4]   Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides [J].
Dong, Dao-Qing ;
Han, Qing-Qing ;
Yang, Shao-Hui ;
Song, Jing-Cheng ;
Li, Na ;
Wang, Zu-Li ;
Xu, Xin-Ming .
CHEMISTRYSELECT, 2020, 5 (42) :13103-13134
[5]   Photoredox-catalyzed coupling of CO2 reduction and amines oxidation by Cu doped CdS quantum dots [J].
Gao, Long-Hui ;
Xiao, Wei-Yun ;
Qi, Ming-Yu ;
Li, Jing-Yu ;
Tan, Chang-Long ;
Tang, Zi-Rong .
MOLECULAR CATALYSIS, 2024, 554
[6]   Visible-light-initiated tandem synthesis of difluoromethylated oxindoles in 2-MeTHF under additive-, metal catalyst-, external photosensitizer-free and mild conditions [J].
Gui, Qing-Wen ;
Teng, Fan ;
Li, Zhou-Chao ;
Xiong, Zhi-Yuan ;
Jin, Xue-Feng ;
Lin, Ying-Wu ;
Cao, Zhong ;
He, Wei-Min .
CHINESE CHEMICAL LETTERS, 2021, 32 (06) :1907-1910
[7]   BOND-FORMING INITIATION IN SPONTANEOUS ADDITION AND POLYMERIZATION REACTIONS OF ALKENES [J].
HALL, HK .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (06) :440-455
[8]   Persulfate promoted tandem radical cyclization of ortho-cyanoarylacrylamides with oxamic acids for construction of carbamoyl quinoline-2,4-diones under metal-free conditions [J].
Han, Qing-Qing ;
Sun, Yuan-Yuan ;
Yang, Shao-Hui ;
Song, Jing-Cheng ;
Wang, Zu-Li .
CHINESE CHEMICAL LETTERS, 2021, 32 (11) :3632-3635
[9]   Seminormal-BrCH2CH2OH-mediated electrochemical epoxidation of unactivated olefins [J].
He, Hong ;
Lv, Yanxia ;
Hu, Jing ;
Hou, Zhong-Wei ;
Wang, Lei .
GREEN CHEMISTRY, 2024, 26 (04) :2157-2161
[10]   Chlorophyll b-modified TiO2 nanoparticles for visible-light-induced photocatalytic synthesis of new tetrahydroquinoline derivatives [J].
Heidari, Aida ;
Safa, Kazem D. ;
Teimuri-Mofrad, Reza .
MOLECULAR CATALYSIS, 2023, 547
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