Synthesis of -Ketosulfones by using Sulfonyl Chloride as a Sulfur Source

被引:37
作者
Xia, Yingya [1 ]
Chen, Xiaolan [1 ]
Qu, Lingbo [1 ,2 ]
Sun, Kai [1 ]
Xia, Xiaoyi [1 ]
Fu, Wenkai [1 ]
Chen, Xi [1 ]
Yang, Yongkang [1 ]
Zhao, Yufen [1 ,3 ]
Li, Chaojun [4 ,5 ]
机构
[1] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450052, Peoples R China
[2] Luoyang Inst Sci & Technol, Luoyang 471023, Peoples R China
[3] Xiamen Univ, Dept Chem, Xiamen 361005, Peoples R China
[4] McGill Univ, Dept Chem, Montreal, PQ H3A 0B8, Canada
[5] McGill Univ, FQRNT Ctr Green Chem & Catalysis, Montreal, PQ H3A 0B8, Canada
关键词
alkenes; electrophiles; -ketosulfones; sulfonyl chlorides; BETA-KETO-SULFONES; DEHYDROGENASE TYPE-I; ONE-POT SYNTHESIS; IONIC LIQUID; EFFICIENT; DERIVATIVES; INHIBITORS; DIOXYGEN; STRATEGY; ALKYNES;
D O I
10.1002/ajoc.201600205
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient one-pot green strategy has been developed for the synthesis of -ketosulfones by directly using easily available and inexpensive sulfonyl chlorides as a sulfur source to react with aromatic alkenes in the presence of cheap tert-butyl hydroperoxide (TBHP) and Et3N in 1,2-dichloroethane (DCE) at 45 degrees C within 3h.
引用
收藏
页码:878 / 881
页数:4
相关论文
共 31 条
[1]  
[Anonymous], 2014, ANGEW CHEM, V126, P4289
[2]   AN EXPEDIENT SYNTHESIS OF TRISUBSTITUTED ALLENES [J].
BALDWIN, JE ;
ADLINGTON, RM ;
CROUCH, NP ;
HILL, RL ;
LAFFEY, TG .
TETRAHEDRON LETTERS, 1995, 36 (43) :7925-7928
[3]   SYNTHESIS OF ACETYLENES FROM CARBOXYLIC-ACID DERIVATIVES VIA BETA-KETO SULFONES [J].
BARTLETT, PA ;
GREEN, FR ;
ROSE, EH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (15) :4852-4858
[4]   A one-pot strategy to synthesize β-ketophosphonates: silver/copper catalyzed direct oxyphosphorylation of alkynes with H-phosphonates and oxygen in the air [J].
Chen, Xin ;
Li, Xu ;
Chen, Xiao-Lan ;
Qu, Ling-Bo ;
Chen, Jian-Yu ;
Sun, Kai ;
Liu, Zhi-Dong ;
Bi, Wen-Zhu ;
Xia, Ying-Ya ;
Wu, Hai-Tao ;
Zhao, Yu-Fen .
CHEMICAL COMMUNICATIONS, 2015, 51 (18) :3846-3849
[5]   Rapid synthesis of sulfone derivatives as potential anti-infectious agents [J].
Curti, C. ;
Laget, M. ;
Carle, A. Ortiz ;
Gellis, A. ;
Vanelle, P. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2007, 42 (06) :880-884
[6]   CuI catalyzed sulfonylation of organozinc reagents with sulfonyl halides [J].
Fu, Ying ;
Zhu, Wenbo ;
Zhao, Xingling ;
Huegel, Helmut ;
Wu, Zhouqiang ;
Su, Yuhu ;
Du, Zhengyin ;
Huang, Danfeng ;
Hu, Yulai .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (25) :4295-4299
[7]   Efficient conversion of sulfones into β-keto sulfones by N-acylbenzotriazoles [J].
Katritzky, AR ;
Abdel-Fattah, AAA ;
Wang, MY .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1443-1446
[8]   1-Butyl-3-methylimidazolium p-toluenesulfinate: a novel reagent for synthesis of sulfones and β-ketosulfones in ionic liquid [J].
Kumar, Anil ;
Muthyala, Manoj Kumar .
TETRAHEDRON LETTERS, 2011, 52 (41) :5368-5370
[9]   A facile one-pot synthesis of β-keto sulfones from ketones under solvent-free conditions [J].
Kumar, Dalip ;
Rao, V. S. ;
Varma, Rajender S. .
TETRAHEDRON LETTERS, 2006, 47 (25) :4197-4199
[10]   α-Fluorination of β-ketosulfones by Selectfluor™ F-TEDA-BF4 [J].
Loghmani-Khouzani, Hossein ;
Poorheravi, Mohammad R. ;
Sadeghi, Majid M. M. ;
Caggiano, Lorenzo ;
Jackson, Richard F. W. .
TETRAHEDRON, 2008, 64 (30-31) :7419-7425