Rh(iii)-Catalyzed -fluoroalkenylation of N-nitrosoanilines with 2,2-difluorovinyl tosylates via C-H bond activation

被引:43
作者
Tian, Miaomiao [1 ]
Yang, Xifa [2 ]
Zhang, Bo [1 ]
Liu, Bingxian [1 ]
Li, Xingwei [1 ,2 ,3 ]
机构
[1] Henan Normal Univ, Sch Chem & Chem Engn, Henan Key Lab Organ Funct Mol & Drug Innovat, Xinxiang 453007, Peoples R China
[2] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[3] Shaanxi Normal Univ, Sch Chem & Chem Engn, Xian 710119, Shaanxi, Peoples R China
关键词
ALPHA-FLUOROALKENYLATION; FLUORINE; ARENES; CATALYSIS; NITROSO; FUNCTIONALIZATIONS; PHARMACEUTICALS; FLUOROOLEFINS; INHIBITORS; INDOLES;
D O I
10.1039/c8qo00947c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rh(iii)-Catalyzed -fluoroalkenylation of N-nitrosoanilines with 2,2-difluorovinyl tosylates has been realized. This reaction proceeded via chelation-assisted C-H activation, olefin insertion and -F elimination, leading to the synthesis of monofluoroalkenes with high Z-selectivity with respect to the olefin. This catalytic system is highly efficient over a broad range of substrates under mild and redox-neutral conditions.
引用
收藏
页码:3406 / 3409
页数:4
相关论文
共 58 条
[1]   C-H Bond Activation by f-Block Complexes [J].
Arnold, Polly L. ;
McMullon, Max W. ;
Rieb, Julia ;
Kuehn, Fritz E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (01) :82-100
[2]   Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom [J].
Babudri, Francesco ;
Farinola, Gianluca M. ;
Naso, Francesco ;
Ragni, Roberta .
CHEMICAL COMMUNICATIONS, 2007, (10) :1003-1022
[3]   Organic fluorine compounds: a great opportunity for enhanced materials properties [J].
Berger, Ricarda ;
Resnati, Giuseppe ;
Metrangolo, Pierangelo ;
Weber, Edwin ;
Hulliger, Juerg .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3496-3508
[4]   Manganese-catalyzed synthesis of monofluoroalkenes via C-H activation and C-F cleavage [J].
Cai, Sai-Hu ;
Ye, Lu ;
Wang, Ding-Xing ;
Wang, Yi-Qiu ;
Lai, Lin-Jie ;
Zhu, Chuan ;
Feng, Chao ;
Loh, Teck-Peng .
CHEMICAL COMMUNICATIONS, 2017, 53 (62) :8731-8734
[5]   Monofluorination of Organic Compounds: 10 Years of Innovation [J].
Champagne, Pier Alexandre ;
Desroches, Justine ;
Hamel, Jean-Denys ;
Vandamme, Mathilde ;
Paquin, Jean-Francois .
CHEMICAL REVIEWS, 2015, 115 (17) :9073-9174
[6]   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
[7]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
[8]   Chiral dipeptide mimics possessing fluoroolefin moiety: a relevant tool for conformational and medicinal studies [J].
Couve-Bonnaire, Samuel ;
Cahard, Dominique ;
Pannecoucke, Xavier .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (08) :1151-1157
[9]   Rhodium(III)-Catalyzed Direct Cyanation of Aromatic C-H Bond to Form 2-(Alkylamino)benzonitriles Using N-Nitroso As Directing Group [J].
Dong, Jiawei ;
Wu, Zhongjie ;
Liu, Zhengyi ;
Liu, Ping ;
Sun, Peipei .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24) :12588-12593
[10]   Fluoroolefins as amide bond mimics in dipeptidyl peptidase IV inhibitors [J].
Edmondson, Scott D. ;
Wei, Lan ;
Xu, Jinyou ;
Shang, Jackie ;
Xu, Shiyao ;
Pang, Jianmei ;
Chaudhary, Ashok ;
Dean, Dennis C. ;
He, Huaibing ;
Leiting, Barbara ;
Lyons, Kathryn A. ;
Patel, Reshma A. ;
Patel, Sangita B. ;
Scapin, Giovanna ;
Wu, Joseph K. ;
Beconi, Maria G. ;
Thornberry, Nancy A. ;
Weber, Ann E. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (07) :2409-2413