Simple and convenient synthesis of fluoroalkenes via direct coupling of alcohols, alkynes and fluoroboric acid under metal-free conditions

被引:13
作者
Yan, Xiao-wei [1 ,2 ]
Zhang, Qiang [1 ]
Wei, Wei [3 ]
Ji, Jian-xin [1 ]
机构
[1] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Qufu Normal Univ, Sch Chem & Chem Engn, Qufu 273165, Shandong, Peoples R China
基金
中国国家自然科学基金;
关键词
Fluoroalkenes; Alkynes; Alcohols; Fluoroboric acid; Metal-free; ANTI-HIV ACTIVITY; STEREOSELECTIVE-SYNTHESIS; BOND FORMATION; EFFICIENT; FLUORINATION; HALIDES;
D O I
10.1016/j.tetlet.2014.05.069
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and convenient method for the synthesis of fluoroalkenes from alkynes, alcohols and fluoroboric acid has been developed under mild conditions. The present protocol provides an attractive approach to access various fluoroalkenes from simple and commercially available starting materials without any metal catalyst, ligand or additive. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3750 / 3752
页数:3
相关论文
共 44 条
[1]   Reversible C-F bond formation and the Au-catalyzed hydrofluorination of alkynes [J].
Akana, Jennifer A. ;
Bhattacharyya, Koyel X. ;
Mueller, Peter ;
Sadighi, Joseph P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (25) :7736-+
[2]   Synthesis and antibacterial activity of 1-(2-fluorovinyl)-7-substituted-4-quinolone-3-carboxylic acid derivatives, conformationally restricted analogues of fleroxacin [J].
Asahina, Y ;
Iwase, K ;
Iinuma, F ;
Hosaka, M ;
Ishizaki, T .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (09) :3194-3202
[3]   Synthesis of quaternary amino acids bearing a (2′Z)-fluorovinyl α-branch:: Potential PLP enzyme inactivators [J].
Berkowitz, DB ;
de la Salud-Bea, R ;
Jahng, WJ .
ORGANIC LETTERS, 2004, 6 (11) :1821-1824
[4]   New and Efficient Iron Halide Mediated Synthesis of Alkenyl Halides through Coupling of Alkynes and Alcohols [J].
Biswas, Srijit ;
Maiti, Sukhendu ;
Jana, Umasish .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (14) :2354-2359
[5]   Synthesis and anti-HIV activity novel nucleoside phosphonate HIV of GS-9148 (2′-Fd4AP), a reverse transcriptase inhibitor [J].
Boojamra, Constantine G. ;
Mackman, Richard L. ;
Markevitch, David Y. ;
Prasad, Vidya ;
Ray, Adrian S. ;
Douglas, Janet ;
Grant, Deborah ;
Kim, Choung U. ;
Cihlar, Tomas .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (03) :1120-1123
[6]   Palladium/copper (I) halide-cocatalyzed stereospecific coupling of 1-fluorovinylstannanes with aryl iodides and acyl chlorides [J].
Chen, C ;
Wilcoxen, K ;
Kim, KI ;
McCarthy, JR .
TETRAHEDRON LETTERS, 1997, 38 (44) :7677-7680
[7]   Stereoselective synthesis and antiviral activity of D-2′,3′-didehydro-2′,3′-dideoxy-2′-fluoro-4′-thionucleosides [J].
Chong, YH ;
Choo, H ;
Choi, Y ;
Mathew, J ;
Schinazi, RF ;
Chu, CK .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (22) :4888-4898
[8]   Stereoselective hydrofluorination of ynamides: a straightforward synthesis of novel α-fluoroenamides [J].
Compain, Guillaume ;
Jouvin, Kevin ;
Martin-Mingot, Agnes ;
Evano, Gwilherm ;
Marrot, Jerome ;
Thibaudeau, Sebastien .
CHEMICAL COMMUNICATIONS, 2012, 48 (42) :5196-5198
[9]   Iodofluorination of alkenes and alkynes promoted by iodine and 4-iodotoluene difluoride [J].
Conte, P ;
Panunzi, B ;
Tingoli, M .
TETRAHEDRON LETTERS, 2006, 47 (03) :273-276
[10]   A new retinoid-like compound that activates peroxisome proliferator-activated receptors and lowers blood glucose in diabetic mice [J].
Deng, T ;
Shan, S ;
Li, ZB ;
Wu, ZW ;
Liao, CZ ;
Ko, B ;
Lu, XP ;
Cheng, J ;
Ning, ZQ .
BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2005, 28 (07) :1192-1196