Photoredox Defluorinative Alkylation of 1-Trifluoromethyl Alkenes and 1,3-Butadienes with 1,4-Dihydropyridines as Alkylation Reagents

被引:53
作者
Chen, Haoguo [1 ]
Anand, Devireddy [1 ]
Zhou, Lei [1 ]
机构
[1] Sun Yat Sen Univ, Sch Chem, 135 Xingang West Rd, Guangzhou 510275, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
alkylation; C-F bond cleavage; difluoroalkenes; photoredox; radicals; NUCLEOPHILIC 5-ENDO-TRIG CYCLIZATION; GEM-DIFLUOROALKENES; ADDITION-REACTION; RADICAL-ADDITION; ALPHA; FLUORINE; 4-ALKYL-1,4-DIHYDROPYRIDINES; FUNCTIONALIZATION; ELIMINATION; ESTERS;
D O I
10.1002/ajoc.201900026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A radical defluorinative alkylation method of 1-trifluoromethyl alkenes and 1,3-butadienes with 4-alkyl-1,4-dihydropyridines under visible light irradiation is presented. Various alkylated 1,1-difluoroalkenes and 1,1-difluorodienes were obtained in moderate to high yields through a sequential C-C and C-F bond cleavage process.
引用
收藏
页码:661 / 664
页数:4
相关论文
共 56 条
[41]   Visible-Light-Mediated Aromatic Substitution Reactions of Cyanoarenes with 4-Alkyl-1,4-dihydropyridines through Double Carbon-Carbon Bond Cleavage [J].
Nakajima, Kazunari ;
Nojima, Sunao ;
Sakata, Ken ;
Nishibayashi, Yoshiaki .
CHEMCATCHEM, 2016, 8 (06) :1028-1032
[42]   Radical addition reaction of 2-benzoyloxypentafluoropropene onto cycloalkanes [J].
Narita, T ;
Hagiwara, T ;
Hamana, H ;
Kitamura, K ;
Inagaki, Y ;
Yoshida, Y .
JOURNAL OF FLUORINE CHEMISTRY, 1999, 97 (1-2) :263-265
[43]   Exploiting the unusual effects of fluorine in methodology [J].
Orsi, Douglas L. ;
Altman, Ryan A. .
CHEMICAL COMMUNICATIONS, 2017, 53 (53) :7168-7181
[44]   Chemistry of fluorinated enamines. Novel reaction of trifluoromethylated enamine with Grignard reagents [J].
Park, HM ;
Uegaki, T ;
Konno, T ;
Ishihara, T ;
Yamanaka, H .
TETRAHEDRON LETTERS, 1999, 40 (15) :2985-2988
[45]  
Takeda T., 2004, MODERN CARBONYL OLEF
[46]   Direct Stereoselective Installation of Alkyl Fragments at the β-Carbon of Enals via Excited Iminium Ion Catalysis [J].
Verrier, Charlie ;
Alandini, Nurtalya ;
Pezzetta, Cristofer ;
Moliterno, Mauro ;
Buzzetti, Luca ;
Hepburn, Hamish B. ;
Vega-Penaloza, Alberto ;
Silvi, Mattia ;
Melchiorre, Paolo .
ACS CATALYSIS, 2018, 8 (02) :1062-1066
[47]   Enantioselective Copper-Catalyzed Defluoroalkylation Using Arylboronate-Activated Alkyl Grignard Reagents [J].
Wang, Minyan ;
Pu, Xinghui ;
Zhao, Yunfei ;
Wang, Panpan ;
Li, Zexian ;
Zhu, Chendan ;
Shi, Zhuangzhi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (29) :9061-9065
[48]   REACTION OF ALPHA-TRIFLUOROMETHYLACRYLIC ACID WITH VARIOUS UNSATURATED GRIGNARD-REAGENTS [J].
WATANABE, S ;
SUGAHARA, K ;
FUJITA, T ;
SAKAMOTO, M ;
KITAZUME, T .
JOURNAL OF FLUORINE CHEMISTRY, 1993, 62 (2-3) :201-206
[49]   Synthesis of 21,21-difluoro-3β-hydroxy-20-methylpregna-5,20-diene and 5,16,20-triene as potential inhibitors of steroid C17(20) lyase [J].
Weintraub, PM ;
Holland, AK ;
Gates, CA ;
Moore, WR ;
Resvick, RJ ;
Bey, P ;
Peet, NP .
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (03) :427-431
[50]   Visible Light-Mediated Trifluoromethylation of Fluorinated Alkenes via C-F Bond Cleavage [J].
Wu, Liu-Hai ;
Cheng, Jun-Kee ;
Shen, Liang ;
Shen, Zhi-Liang ;
Loh, Teck-Peng .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (20) :3894-3899