Synthesis and Cross-Coupling of Sulfonamidomethyltrifluoroborates

被引:29
作者
Molander, Gary A. [1 ]
Fleury-Bregeot, Nicolas [1 ]
Hiebel, Marie-Aude [1 ]
机构
[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA
关键词
HALO BORONIC ESTERS; SULFONAMIDES; DISCOVERY; POTENT; AMINOMETHYLATIONS; DERIVATIVES; ANTICANCER; ALKYL;
D O I
10.1021/ol200202g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sulfonamidomethyltrifluoroborates were successfully synthesized and cross-coupled with a wide range of aryl and heteroaryl chlorides, allowing the construction of a sulfonamidomethyl aryl linkage through a new disconnection, thus offering a new way to access such structurally interesting motifs.
引用
收藏
页码:1694 / 1697
页数:4
相关论文
共 45 条
[1]   Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].
AbdelMagid, AF ;
Carson, KG ;
Harris, BD ;
Maryanoff, CA ;
Shah, RD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862
[2]   Sulfonamide drugs binding to the colchicine site of tubulin: Thermodynamic analysis of the drug-tubulin interactions by isothermal titration calorimetry [J].
Banerjee, M ;
Poddar, A ;
Mitra, G ;
Surolia, A ;
Owa, T ;
Bhattacharyya, B .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (02) :547-555
[3]   B(C6F5)3-catalyzed hydrosilation of imines via silyliminium intermediates [J].
Blackwell, JM ;
Sonmor, ER ;
Scoccitti, T ;
Piers, WE .
ORGANIC LETTERS, 2000, 2 (24) :3921-3923
[4]  
BLADH H, 2006, Patent No. 2006046914
[5]   Aryl Trifluoroborates in Suzuki-Miyaura Coupling: The Roles of Endogenous Aryl Boronic Acid and Fluoride [J].
Butters, Mike ;
Harvey, Jeremy N. ;
Jover, Jesus ;
Lennox, Alastair J. J. ;
Lloyd-Jones, Guy C. ;
Murray, Paul M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (30) :5156-5160
[6]   Direct synthesis of sulfonamides and activated sulfonate esters from sulfonic acids [J].
Caddick, S ;
Wilden, JD ;
Judd, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (04) :1024-1025
[7]   Solid-phase intermolecular radical reactions 2:: Synthesis of C-glycopeptide mimetics via a novel acrylate acceptor [J].
Caddick, S ;
Hamza, D ;
Wadman, SN ;
Wilden, JD .
ORGANIC LETTERS, 2002, 4 (10) :1775-1777
[8]   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
[9]   Metal-free catalytic hydrogenation [J].
Chase, Preston A. ;
Welch, Gregory C. ;
Jurca, Titel ;
Stephan, Douglas W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (42) :8050-8053
[10]   Discovery of 5-arylsulfonamido-3(pyrrolidin-2-ylmethyl)-1H-indole derivatives as potent, selective 5-HT6 receptor agonists and antagonists [J].
Cole, DC ;
Lennox, WJ ;
Lombardi, S ;
Ellingboe, JW ;
Bernotas, RC ;
Tawa, GJ ;
Mazandarani, H ;
Smith, DL ;
Zhang, GM ;
Coupet, J ;
Schechter, LE .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (02) :353-356