Tributyltin hydride and 1-ethylpiperidine hypophosphite mediated intermolecular radical additions to 2,4,6-trichlorophenyl vinyl sulfonate

被引:7
作者
Edetanlen-Elliot, Oluwabusola [1 ]
Fitzmaurice, Richard J. [1 ]
Wilden, Jonathan D. [1 ]
Caddick, Stephen [1 ]
机构
[1] UCL, Christopher Ingold Labs, Dept Chem, London WC1H 0AJ, England
基金
英国工程与自然科学研究理事会; 英国生物技术与生命科学研究理事会;
关键词
radical addition; tributyltin hydride; EPHP; TCP-sulfonate; sulfonamide;
D O I
10.1016/j.tetlet.2007.10.030
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2,4,6-Trichlorophenyl vinyl sulfonate smoothly undergoes intermolecular radical addition under mild initiation conditions mediated by tributyltin hydride and 1-ethylpiperidine hypophosphite (EPHP) to generate a range of functionalised alkyl sulfonamide precursors. This methodology can be used to prepare bifunctional pentafluorophenyl/2,4,6-trichlorophenyl sulfonates in good yields. (c) 2007 Published by Elsevier Ltd.
引用
收藏
页码:8926 / 8929
页数:4
相关论文
共 12 条
[1]   A novel route to functionalized PFP esters via rapid intermolecular radical addition to PFP acrylate mediated by ethylpiperidinium hypophosphite (EPHP) [J].
Caddick, S ;
Hamza, D ;
Judd, DB ;
Reich, MT ;
Wadman, SN ;
Wilden, JD .
TETRAHEDRON LETTERS, 2004, 45 (11) :2363-2366
[2]   A new route to sulfonamides via intermolecular radical addition to pentafluorophenyl vinylsulfonate and subsequent aminolysis [J].
Caddick, S ;
Wilden, JD ;
Bush, HD ;
Wadman, SN ;
Judd, DB .
ORGANIC LETTERS, 2002, 4 (15) :2549-2551
[3]   A facile, environmentally benign sulfonamide synthesis in water [J].
Deng, Xiaohu ;
Mani, Neelakandha S. .
GREEN CHEMISTRY, 2006, 8 (09) :835-838
[4]   KF-silica as a stationary phase for the chromatographic removal of tin residues from organic compounds [J].
Harrowven, DC ;
Guy, IL .
CHEMICAL COMMUNICATIONS, 2004, (17) :1968-1969
[5]   Azithromycin-sulfonamide conjugates as inhibitors of resistant Streptococcus pyogenes strains [J].
Krajacic, Mirjana Bukvic ;
Novak, Predrag ;
Cindric, Mario ;
Brajsa, Karmen ;
Dumic, Mijenko ;
Kujundzic, Nedjeljko .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2007, 42 (02) :138-145
[6]   Synthesis and evaluation of galactofuranosyl N,N-dialkyl sulfenamides and sulfonamides as antimycobacterial agents [J].
Owen, David J. ;
Davis, Chris B. ;
Hartnell, Regan D. ;
Madge, Paul D. ;
Thomson, Robin J. ;
Chong, Andrew K. J. ;
Coppel, Ross L. ;
von Itzstein, Mark .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (08) :2274-2277
[7]   Facile one-pot synthesis of aromatic and heteroaromatic sulfonamides [J].
Pandya, R ;
Murashima, T ;
Tedeschi, L ;
Barrett, AGM .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (21) :8274-8276
[8]   Synthesis and selected reactions of a bicyclic sultam having sulfur at the apex position [J].
Preston, Adam J. ;
Gallucci, Judith C. ;
Paquette, Leo A. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17) :6573-6578
[9]   Anticancer and antiviral sulfonamides [J].
Scozzafava, A ;
Owa, T ;
Mastrolorenzo, A ;
Supuran, CT .
CURRENT MEDICINAL CHEMISTRY, 2003, 10 (11) :925-953
[10]   Dipeptide vinyl sultams:: Synthesis via the Wittig-Horner reaction and activity against papain, falcipain-2 and Plasmodium falciparum [J].
Valente, Claudia ;
Guedes, Rita C. ;
Moreira, Rui ;
Iley, Jim ;
Gut, Jiri ;
Rosenthal, Philip J. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (15) :4115-4119