Visible light-promoted umpolung coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines

被引：24
作者：
Xu, Xiao [1 ,2 ]
Min, Qing-Qiang [1 ,2 ]
Li, Na [1 ,2 ]
Liu, Feng [1 ,2 ,3 ]
机构：
[1] Soochow Univ, Coll Pharmaceut Sci, Jiangsu Key Lab Neuropsychiat Dis, 199 Ren Ai Rd, Suzhou 215123, Jiangsu, Peoples R China
[2] Soochow Univ, Coll Pharmaceut Sci, Dept Med Chem, 199 Ren Ai Rd, Suzhou 215123, Jiangsu, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 78期
基金：
中国国家自然科学基金;
关键词：
PHOTOREDOX CATALYSIS; ORGANOFLUORINE CHEMISTRY; SYNTHETIC APPLICATIONS; CARBONYL DERIVATIVES; MEDICINAL CHEMISTRY; ACTIVATING GROUPS; KETONES; ALDEHYDES; IMINES; PHARMACEUTICALS;
D O I：
10.1039/c8cc06748a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Tertiary alcohols bearing a trifluoromethyl group are of considerable medicinal interest. Using an umpolung strategy, we herein report the first intermolecular reductive cross-coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines with the aid of a BrOnsted acid catalyst upon visible-light irradiation. This metal-free reaction is operationally simple and performed at ambient temperature, allowing access to desired tertiary alcohols with tri-/difluoromethyl groups in moderate to excellent yields. The commercially available and easily handled Hantzsch ester effectively serves as an electron donor, as well as a hydrogen atom source.
引用
收藏
页码：11017 / 11020
页数：4
相关论文
共 42 条
[1]   Enantioselective Photocatalytic [3+2] Cycloadditions of Aryl Cyclopropyl Ketones [J].
Amador, Adrian G. ;
Sherbrook, Evan M. ;
Yoon, Tehshik P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (14) :4722-4725
[2]   C=N-Containing Azaarenes as Activating Groups in Enantioselective Catalysis [J].
Best, Daniel ;
Lam, Hon Wai .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (03) :831-845
[3]   Evolution of the stereoselective pinacol coupling reaction [J].
Chatterjee, A. ;
Joshi, N. N. .
TETRAHEDRON, 2006, 62 (52) :12137-12158
[4]   Phosphine-Catalyzed Aza-MBH Reactions of Vinylpyridines: Efficient and Rapid Access to 2,3,5-Triarylsubstituted 3-Pyrrolines [J].
Chen, Jing ;
Li, Jianjun ;
Wang, Jiazhe ;
Li, Hao ;
Wang, Wei ;
Guo, Yuewei .
ORGANIC LETTERS, 2015, 17 (09) :2214-2217
[5]   Enantioselective Copper-Catalyzed Reductive Coupling of Vinylazaarenes with N-Boc Aldimines [J].
Choi, Bonnie ;
Saxenaa, Aakarsh ;
Smith, Joshua J. ;
Churchill, Gwydion H. ;
Lam, Hon Wai .
SYNLETT, 2015, 26 (03) :350-354
[6]   Reductive Umpolung of Carbonyl Derivatives with Visible-Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α-Amino Radicals and Ketyl Radicals [J].
Fava, Eleonora ;
Millet, Anthony ;
Nakajima, Masaki ;
Loescher, Sebastian ;
Rueping, Magnus .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (23) :6776-6779
[7]   Discovery of pyridine-based agrochemicals by using Intermediate Derivatization Methods [J].
Guan, Ai-Ying ;
Liu, Chang-Ling ;
Sun, Xu-Feng ;
Xie, Yong ;
Wang, Ming-An .
BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (03) :342-353
[8]   Selective difluoromethylation and monofluoromethylation reactions [J].
Hu, Jinbo ;
Zhang, Wei ;
Wang, Fei .
CHEMICAL COMMUNICATIONS, 2009, (48) :7465-7478
[9]   Selective Radical-Radical Cross-Couplings: Design of a Formal β-Mannich Reaction [J].
Jeffrey, Jenna L. ;
Petronijevic, Filip R. ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (26) :8404-8407
[10]   Selective Debromination and α-Hydroxylation of α-Bromo Ketones Using Hantzsch Esters as Photoreductants [J].
Jung, Jaehun ;
Kim, Jun ;
Park, Gyurim ;
You, Youngmin ;
Cho, Eun Jin .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (01) :74-80
12345