Copper-Mediated Sulfonylation of Aryl C(sp2)-H Bonds with Sodium and Lithium Sulfinates

被引:48
作者
Liang, Shuai [1 ]
Liu, Nai-Wei [1 ]
Manolikakes, Georg [1 ]
机构
[1] Goethe Univ Frankfurt, Dept Organ Chem & Chem Biol, Max von Laue Str 7, D-60438 Frankfurt, Germany
关键词
amide-oxazolines; C-H activation; copper; sulfinates; sulfonylation; UNSYMMETRICAL DIARYL SULFONES; C-H BONDS; ACID SALTS; FUNCTIONALIZATION; HALIDES; ARENES; MECHANISM; INDOLES; ACCESS;
D O I
10.1002/adsc.201500793
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A copper-mediated direct sulfonylation of aryl C(sp(2))-H bonds with sodium and lithium sulfinates is reported. Various aryl sulfones were synthesized in moderate to excellent yields with good functional group tolerance.
引用
收藏
页码:159 / 163
页数:5
相关论文
共 47 条
[1]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[2]   Metal-free, high yielding synthesis of unsymmetrical biaryl, bi(heteroaryl), aryl vinyl, aryl alkyl sulfones via coupling of aryne with sulfinic acid salts [J].
Aithagani, Sravan Kumar ;
Yempalla, Kushalava Reddy ;
Munagala, Gurunadham ;
Vishwakarma, Ram A. ;
Singh, Parvinder Pal .
RSC ADVANCES, 2014, 4 (91) :50208-50211
[3]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[4]   Unsymmetrical diaryl Sulfones through palladium-catalyzed coupling of aryl boronic acids and arylsulfonyl chlorides [J].
Bandgar, BP ;
Bettigeri, SV ;
Phopase, J .
ORGANIC LETTERS, 2004, 6 (13) :2105-2108
[5]   An efficient copper catalyst for the formation of sulfones from sulfinic acid salts and aryl iodides [J].
Baskin, JM ;
Wang, ZY .
ORGANIC LETTERS, 2002, 4 (25) :4423-4425
[6]   Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].
Beletskaya, Irina P. ;
Ananikov, Valentine P. .
CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636
[7]   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
[8]   Unsymmetrical diaryl sulfones through palladium-catalyzed coupling of aryl iodides and arenesulfinates [J].
Cacchi, S ;
Fabrizi, G ;
Goggiamani, A ;
Parisi, LM .
ORGANIC LETTERS, 2002, 4 (26) :4719-4721
[9]   A one-pot regioselective synthetic route to vinyl sulfones from terminal epoxides in aqueous media [J].
Chawla, Ruchi ;
Kapoor, Ritu ;
Singh, Atul K. ;
Yadav, Lal Dhar S. .
GREEN CHEMISTRY, 2012, 14 (05) :1308-1313
[10]  
Clayden J., 2002, ORGANOLITHIUM SELECT