Rhodium(III)-Catalyzed Ortho Halogenations of N-Acylsulfoximines and Synthetic Applications toward Functionalized Sulfoximine Derivatives

被引:46
作者
Cheng, Ying [1 ]
Dong, Wanrong [1 ]
Parthasarathy, Kanniyappan [1 ]
Bolm, Carsten [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany
关键词
C-H FUNCTIONALIZATION; BOND FUNCTIONALIZATIONS; ORTHO-BROMINATION; IODINATION; (HETERO)ARENES; CHLORINATION;
D O I
10.1021/acs.orglett.7b00043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodium(III)-catalyzed ortho brominations and iodinations of N-acylsulfoximines by C-H bond activations have been developed. Subsequent product functionalizations involving cross-coupling reactions provide alkynylated sulfoximine derivatives and benzothiazines with wide potential for further synthetic applications.
引用
收藏
页码:726 / 729
页数:4
相关论文
共 68 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]  
[Anonymous], 2003, CHEMTRACTS
[3]   Mild C-H Halogenation of Anilides and the Isolation of an Unusual Palladium(I)-Palladium(II) Species [J].
Bedford, Robin B. ;
Haddow, Mairi F. ;
Mitchell, Charlotte J. ;
Webster, Ruth L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (24) :5524-5527
[4]   Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].
Chen, Xiao ;
Hao, Xue-Shi ;
Goodhue, Charles E. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791
[5]   Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups [J].
Chen, Zhengkai ;
Wang, Binjie ;
Zhang, Jitan ;
Yu, Wenlong ;
Liu, Zhanxiang ;
Zhang, Yuhong .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09) :1107-1295
[6]   Regioselective Syntheses of 1,2-Benzothiazines by Rhodium-Catalyzed Annulation Reactions [J].
Cheng, Ying ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (42) :12349-12352
[7]   Ruthenium- and palladium-catalyzed consecutive coupling and cyclization of aromatic sulfoximines with phenylboronic acids: an efficient route to dibenzothiazines [J].
Chinnagolla, Ravi Kiran ;
Vijeta, Arjun ;
Jeganmohan, Masilamani .
CHEMICAL COMMUNICATIONS, 2015, 51 (65) :12992-12995
[8]   Synthesis and palladium-catalyzed coupling reactions of enantiopure p-bromophenyl methyl sulfoximine [J].
Cho, GY ;
Okamura, H ;
Bolm, C .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2346-2349
[9]   Employing a robustness screen: rapid assessment of rhodium(III)-catalysed C-H activation reactions [J].
Collins, Karl D. ;
Glorius, Frank .
TETRAHEDRON, 2013, 69 (36) :7817-7825
[10]  
Dagani M.J., 2002, ULLMANNS ENCY IND CH