Highly efficient and versatile synthesis of α,α-difluoro-γ-lactams via aminodifluoroalkylation of alkenes

被引:46
作者
Chen, Hongtai [1 ]
Wang, Xiaoyang [1 ]
Guo, Minjie [2 ]
Zhao, Wentao [1 ]
Tang, Xiangyang [1 ]
Wang, Guangwei [1 ,3 ]
机构
[1] Tianjin Univ, Sch Sci, Dept Chem, Tianjin 300072, Peoples R China
[2] Tianjin Univ, Sch Pharmaceut Sci & Technol, Inst Mol Design & Synth, Tianjin 300072, Peoples R China
[3] Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China
关键词
GAMMA-LACTAMS; INTRAMOLECULAR HYDROAMINATION; UNACTIVATED ALKENES; H FUNCTIONALIZATION; MEDICINAL CHEMISTRY; PART; BOND; AMINOTRIFLUOROMETHYLATION; CATALYSIS; FLUORINE;
D O I
10.1039/c7qo00611j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel method for the synthesis of alpha,alpha-difluoro-gamma-lactam derivatives has been developed using a copper/amine catalyst via a tandem radical cyclization pathway. This protocol provides a convenient and straightforward strategy for the rapid construction of various 3,3-difluoro-gamma-lactam moieties from easily available alkenes and N-aryl bromodifluoroacetamide as starting materials under mild reaction conditions.
引用
收藏
页码:2403 / 2407
页数:5
相关论文
共 65 条
[1]  
Belhomme M.-C., 2014, SYNTHESIS-STUTTGART, P1859
[2]   Copper Catalyzed β-Difluoroacetylation of Dihydropyrans and Glycals by Means of Direct C-H Functionalization [J].
Belhomme, Marie-Charlotte ;
Poisson, Thomas ;
Pannecoucke, Xavier .
ORGANIC LETTERS, 2013, 15 (13) :3428-3431
[3]   Recent Progress in Direct Introduction of Fluorinated Groups on Alkenes and Alkynes by means of C-H Bond Functionalization [J].
Besset, Tatiana ;
Poisson, Thomas ;
Pannecoucke, Xavier .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (51) :16830-16845
[4]   Copper-catalyzed olefinic C-H difluoroacetylation of enamides [J].
Caillot, Gilles ;
Dufour, Jeremy ;
Belhomme, Marie-Charlotte ;
Poisson, Thomas ;
Grimaud, Laurence ;
Pannecoucke, Xavier ;
Gillaizeau, Isabelle .
CHEMICAL COMMUNICATIONS, 2014, 50 (44) :5887-5890
[5]   Photoredox-Induced Three-Component Oxy-, Amino-, and Carbotrifluoromethylation of Enecarbamates [J].
Carboni, Aude ;
Dagousset, Guillaume ;
Magnier, Emmanuel ;
Masson, Geraldine .
ORGANIC LETTERS, 2014, 16 (04) :1240-1243
[6]   Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents [J].
Charpentier, Julie ;
Frueh, Natalja ;
Togni, Antonio .
CHEMICAL REVIEWS, 2015, 115 (02) :650-682
[7]   Fluorination-free synthesis of a 4,4-difluoro-3,3-dimethylproline derivative [J].
Chen, Lijian ;
Kim, Young Mi ;
Kucera, David J. ;
Harrison, Katheryn E. ;
Bahmanyar, Sogole ;
Scott, Jill M. ;
Yazbeck, Daniel .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (15) :5468-5473
[8]  
Chen P., 2013, SYNTHESIS-STUTTGART, P2919
[9]  
Chu L., 2014, QING ACC CHEM RES, V47, P1513
[10]   Photoinduced Ullmann C-N Coupling: Demonstrating the Viability of a Radical Pathway [J].
Creutz, Sidney E. ;
Lotito, Kenneth J. ;
Fu, Gregory C. ;
Peters, Jonas C. .
SCIENCE, 2012, 338 (6107) :647-651