A simple guide for predicting regioselectivity in the coupling of polyhaloheteroaromatics

被引:120
作者
Handy, ST [1 ]
Zhang, YN
机构
[1] Middle Tennessee State Univ, Dept Chem, Murfreesboro, TN 37132 USA
[2] Univ Binghamton, Dept Chem, Binghamton, NY 13902 USA
关键词
D O I
10.1039/b512948f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple guide for predicting the order and site of coupling (Suzuki, Stille, Negishi, Sonogashira, etc.) in polyhaloheteroaromatics based upon the H-l NMR chemical shift values of the parent non-halogenated heteroaromatics has been developed.
引用
收藏
页码:299 / 301
页数:3
相关论文
共 31 条
[1]  
Bach T, 1998, SYNLETT, P1185
[2]   Synthesis of eupomatenoids by three consecutive transition metal-catalyzed cross-coupling reactions [J].
Bach, T ;
Bartels, M .
TETRAHEDRON LETTERS, 2002, 43 (50) :9125-9127
[3]   Synthesis of 2′-substituted 4-bromo-2,4′-bithiazoles by regioselective cross-coupling reactions [J].
Bach, T ;
Heuser, S .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5789-5795
[4]  
Bach T, 1999, EUR J ORG CHEM, V1999, P2045
[5]   Synthesis of 2-(o-hydroxyaryl)-4-arylthiazoles by regioselective Pd(0)-catalyzed cross-coupling [J].
Bach, T ;
Heuser, S .
TETRAHEDRON LETTERS, 2000, 41 (11) :1707-1710
[6]   Sequential Pd(0)-catalyzed reactions for the construction of multiple substituted furans.: A short synthesis of the F5 furan fatty acid [J].
Bach, T ;
Krüger, L .
TETRAHEDRON LETTERS, 1998, 39 (13) :1729-1732
[7]   3-[(2-methyl-1,3-thiazol-4-yl)ethynyl]-pyridine: A potent and highly selective metabotropic glutamate subtype 5 receptor antagonist with anxiolytic activity [J].
Cosford, NDP ;
Tehrani, L ;
Roppe, J ;
Schweiger, E ;
Smith, ND ;
Anderson, J ;
Bristow, L ;
Brodkin, J ;
Jiang, XH ;
McDonald, I ;
Rao, S ;
Washburn, M ;
Varney, MA .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (02) :204-206
[8]  
DONDONI A, 1987, SYNTHESIS-STUTTGART, P185
[9]   A concise synthesis of 2,4-disubstituted pyridines: A convenient synthesis of 2-bromo-4-iodopyridine via halogen dance and its successive one-pot disubstitutions [J].
Duan, XF ;
Li, XH ;
Li, FY ;
Huang, CH .
SYNTHESIS-STUTTGART, 2004, (16) :2614-2616
[10]   The mechanisms of the Stille reaction [J].
Espinet, P ;
Echavarren, AM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (36) :4704-4734