Base-promoted synthesis of diarylsulfones from sulfonyl hydrazines and diaryliodonium salts

被引:5
作者
Gong, Bozhen [1 ]
Zhu, Haibo [1 ]
Yang, Liu [1 ]
Wang, Haifeng [1 ,2 ]
Fan, Qiangwen [1 ,3 ]
Xie, Zongbo [1 ]
Le, Zhanggao [1 ]
机构
[1] East China Univ Technol, Sch Chem Biol & Mat Sci, Jiangxi Prov Key Lab Synthet Chem, Nanchang 330013, Jiangxi, Peoples R China
[2] Wuhan Inst Technol, Pharmaceut Res Inst, Wuhan 430205, Peoples R China
[3] East China Univ Technol, Jiangxi Key Lab Mass Spectrometry & Instrumentat, Nanchang 330013, Jiangxi, Peoples R China
基金
中国国家自然科学基金;
关键词
UNSYMMETRICAL DIARYL SULFONES; C-H FUNCTIONALIZATION; METAL-FREE; SULFUR-DIOXIDE; VINYL SULFONES; BOND FORMATION; ARYL HALIDES; SULFIDES; OXIDATION; EFFICIENT;
D O I
10.1039/d2ob00389a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and concise method for the synthesis of diverse substituted sulfones was developed with high selectivity. Using n-PrOH as the solvent, diaryl sulfones are formed even on a gram scale via metal-free coupling from sulfonyl hydrazines with symmetrical or unsymmetrical diaryliodonium salts.
引用
收藏
页码:3501 / 3505
页数:5
相关论文
共 57 条
[1]   Practical oxidation of sulfides to sulfones by H2O2 catalysed by titanium catalyst [J].
Al-Maksoud, Walid ;
Daniele, Stephane ;
Sorokin, Alexander B. .
GREEN CHEMISTRY, 2008, 10 (04) :447-451
[2]   Selective aerobic oxidation of sulfides using a novel palladium complex as the catalyst precursor [J].
Aldea, R ;
Alper, H .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (26) :8365-8366
[3]  
Alex S.D., 2015, ANGEW CHEM-GER EDIT, V55, P747
[4]   Highly selective catalytic Friedel-Crafts sulfonylation of aromatic compounds using a FeCl3-based ionic liquid [J].
Bahrami, Kiumars ;
Khodei, Mohammad Mehdi ;
Shahbazi, Fomeida .
TETRAHEDRON LETTERS, 2008, 49 (24) :3931-3934
[5]   Unsymmetrical diaryl sulfones and aryl vinyl sulfones through palladium-catalyzed coupling of aryl and vinyl halides or triflates with sulfinic acid salts [J].
Cacchi, S ;
Fabrizi, G ;
Goggiamani, A ;
Parisi, LM ;
Bernini, R .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5608-5614
[6]   Soluble Oligo- and Polythienyl Sulfides and Sulfones: Synthesis and Photophysics [J].
Caron, Elise ;
Wolf, Michael O. .
MACROMOLECULES, 2017, 50 (19) :7543-7549
[7]   Copper(I)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling [J].
Chen, Yiding ;
Willis, Michael C. .
CHEMICAL SCIENCE, 2017, 8 (04) :3249-3253
[8]   Imidazole-containing diarylether and diarylsulfone inhibitors of farnesyl-protein transferase [J].
Dinsmore, CJ ;
Williams, TM ;
O'Neill, TJ ;
Liu, DM ;
Rands, E ;
Culberson, JC ;
Lobell, RB ;
Koblan, KS ;
Kohl, NE ;
Gibbs, JB ;
Oliff, AI ;
Graham, SL ;
Hartman, GD .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (23) :3301-3306
[9]   Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry [J].
Feng, Minghao ;
Tang, Bingqing ;
Liang, Steven H. ;
Jiang, Xuefeng .
CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2016, 16 (11) :1200-1216
[10]   Imide-Catalyzed Oxidation System: Sulfides to Sulfoxides and Sulfones [J].
Fukuda, Naohiro ;
Ikemoto, Tomomi .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (13) :4629-4631