Palladium-catalyzed cross-coupling reaction of resin-bound chlorotriazines

被引:33
作者
Bork, JT [1 ]
Lee, JW [1 ]
Chang, YT [1 ]
机构
[1] NYU, Dept Chem, New York, NY 10003 USA
关键词
D O I
10.1016/S0040-4039(03)01451-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
To introduce the biaryl structure as a triazine functionality, we have developed a new synthetic route via the Suzuki cross-coupling reaction of resin-bound chlorotriazines. The Suzuki cross-coupling reaction was achieved using various arylboronic acids, Pd(PPh3)(4), Cs2CO3, and dioxane. With the integration of this chemistry and our previous orthogonal methodology, the triazine library is greatly expanded to a biaryl scaffold. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6141 / 6144
页数:4
相关论文
共 43 条
[1]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ARYLBORONIC ACIDS WITH PI-DEFICIENT HETEROARYL CHLORIDES [J].
ALI, NM ;
MCKILLOP, A ;
MITCHELL, MB ;
REBELO, RA ;
WALLBANK, PJ .
TETRAHEDRON, 1992, 48 (37) :8117-8126
[2]  
Arduengo A. J., 1991, U. S. Patent, Patent No. [5,077,414, 5077414]
[3]   ELECTRONIC STABILIZATION OF NUCLEOPHILIC CARBENES [J].
ARDUENGO, AJ ;
DIAS, HVR ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5530-5534
[4]   Novel orthogonal strategy toward solid-phase synthesis of 1,3,5-substituted triazines [J].
Bork, JT ;
Lee, JW ;
Khersonsky, SM ;
Moon, HS ;
Chang, YT .
ORGANIC LETTERS, 2003, 5 (02) :117-120
[5]   DF-studies on a 'stop and go' rotor: steric and electronic factors determining the regio- and stereochemical position of a eta(6)-Cr(CO)(3) metal fragment on a helically distorted biaryl ligand [J].
Bringmann, G ;
Stowasser, R ;
Gobel, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 544 (01) :7-13
[6]  
Bringmann G, 2001, PROG CH ORG NAT PROD, V82, P1
[7]  
Bringmann G., 1995, ALKALOIDS, V46, P127
[8]   Traceless solid-phase synthesis of 2,6,9-trisubstituted purines from resin bound 6-thiopurines [J].
Brun, V ;
Legraverend, M ;
Grierson, DS .
TETRAHEDRON, 2002, 58 (39) :7911-7923
[9]   Use of the Suzuki reaction for the synthesis of aryl-substituted heterocycles as corticotropin-releasing hormone (CRH) antagonists [J].
Cocuzza, AJ ;
Chidester, DR ;
Culp, S ;
Fitzgerald, L ;
Gilligan, P .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (07) :1063-1066
[10]   Synthesis of 6-aryl-2,4-diamino-pyrimidines and triazines using palladium catalysed Suzuki cross-coupling reactions [J].
Cooke, G ;
de Cremiers, HA ;
Rotello, VM ;
Tarbit, B ;
Vanderstraeten, PE .
TETRAHEDRON, 2001, 57 (14) :2787-2789