Manganese-catalyzed synthesis of monofluoroalkenes via C-H activation and C-F cleavage

被引：102

作者：

Cai, Sai-Hu ^{[1
,2
]}

Ye, Lu ^{[1
]}

Wang, Ding-Xing ^{[1
]}

Wang, Yi-Qiu ^{[1
]}

Lai, Lin-Jie ^{[1
]}

Zhu, Chuan ^{[1
]}

Feng, Chao ^{[1
]}

Loh, Teck-Peng ^{[2
,3
]}

机构：

[1] Nanjing Tech Univ, IAS, Coll Chem & Mol Engn, Jiangsu Natl Synerget Innovat Ctr Adv Mat SICAM, 30 South Puzhu Rd, Nanjing 211800, Jiangsu, Peoples R China

[2] USTC, Dept Chem, 96 Jin Zhai Rd, Hefei 230026, Anhui, Peoples R China

[3] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, SPMS CBC 05-20,21 Nanyang Link, Singapore 637371, Singapore

来源：

CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 62期

关键词：

BOND ACTIVATION; STEREOSELECTIVE-SYNTHESIS; 4+1 ANNULATION; ALKYNES; ACCESS; FLUOROALKENYLATION; FUNCTIONALIZATION; HETEROARENES; ALDEHYDES; ESTERS;

D O I：

10.1039/c7cc04131d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The manganese-catalyzed a-fluoroalkenylation of arenes via C-H activation and C-F cleavage has been described. This protocol provides a very useful method for the synthesis of monofluoroalkenes with predominant unconventional E-isomer selectivity which complements the existing strategies for the access to these molecular architectures. In addition, the selectivity of beta-defluorination in the catalytic cycle not only determines the configurations of the products but also obviates the use of external oxidants, providing a good example in the exploitation of manganese-catalyzed redox-neutral C-H transformations.

引用

页码：8731 / 8734

页数：4

共 56 条

[1] 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

[2] 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

[3] 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

[4] Exploiting 3,3-Difluoropropenes for the Synthesis of Monofluoroalkenes [J].

Drouin, Myriam ;

Hamel, Jean-Denys ;

Paquin, Jean-Francois .

SYNLETT, 2016, 27 (06) :821-830

[5] 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

[6] High-yield synthesis of fluorinated benzothiazolyl sulfones: General synthons for fluoro-julia olefinations [J].

Ghosh, AK ;

Zajc, B .

ORGANIC LETTERS, 2006, 8 (08) :1553-1556

[7] Manganese- Catalyzed Dehydrogenative [4+2] Annulation of N-H Imines and Alkynes by C- H/N- H Activation** [J].

He, Ruoyu ;

Huang, Zhi-Tang ;

Zheng, Qi-Yu ;

Wang, Congyang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (19) :4950-4953

[8] Manganese-catalyzed bicyclic annulations of imines and α,β-unsaturated esters via C-H activation [J].

Hu, Yuanyuan ;

Wang, Congyang .

SCIENCE CHINA-CHEMISTRY, 2016, 59 (10) :1301-1305

[9] n → π☆ Interaction and n)(π Pauli Repulsion Are Antagonistic for Protein Stability [J].

Jakobsche, Charles E. ;

Choudhary, Amit ;

Miller, Scott J. ;

Raines, Ronald T. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (19) :6651-+

[10] Cobalt(III)-Catalyzed Regio- and Stereoselective α-Fluoroalkenylation of Arenes with gem-Difluorostyrenes [J].

Kong, Lingheng ;

Zhou, Xukai ;

Li, Xingwei .

ORGANIC LETTERS, 2016, 18 (24) :6320-6323

← 1 2 3 4 5 6 →