Palladium-catalyzed coupling of vinyl phosphates with aryl or heteroaryl boronic acids. Application to the synthesis of substituted nitrogen containing heterocycles

被引:66
作者
Lepifre, F [1 ]
Clavier, S [1 ]
Bouyssou, P [1 ]
Coudert, G [1 ]
机构
[1] Univ Orleans, CNRS, Inst Chim Organ & Analyt, F-45067 Orleans 02, France
关键词
coupling reactions; palladium and compounds; boronic acids; vinyl phosphates; N-heterocycles;
D O I
10.1016/S0040-4020(01)00651-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Substituted nitrogen-containing heterocycles were prepared in three steps from commercially available derivatives via an extension of the Suzuki reaction involving the palladium-catalyzed coupling of vinyl phosphates with aryl or heteroaryl boronic acids. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6969 / 6975
页数:7
相关论文
共 17 条
[1]   NEW INDOLE-DERIVATIVES - SYNTHESIS OF 3-ACYL-1-CARBETHOXY-2-TRIFLUOROMETHANESULFONYLINDOLES AND OF SUBSTITUTED 2-VINYLINDOLES [J].
BECCALLI, EM ;
MARCHESINI, A .
TETRAHEDRON, 1995, 51 (08) :2353-2362
[2]   Palladium(0)-catalyzed coupling reactions of an N-tosylpyrrolidinone-derived enamine triflate [J].
Bernabe, P ;
Rutjes, FPJT ;
Hiemstra, H ;
Speckamp, WN .
TETRAHEDRON LETTERS, 1996, 37 (20) :3561-3564
[3]   Total synthesis of (+)-aloperine. Use of a nitrogen-bound silicon tether in an intramolecular Diels-Alder reaction [J].
Brosius, AD ;
Overman, LE ;
Schwink, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) :700-709
[4]   PALLADIUM-CATALYZED REDUCTION OF ENOL TRIFLATES TO ALKENES [J].
CACCHI, S ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1984, 25 (42) :4821-4824
[5]   SYNTHESIS AND REACTIONS OF ALPHA-(TRIFLUROMETHANESULFONYLOXY)ENECARBAMATES PREPARED FROM N-ACYLLACTAMS [J].
FOTI, CJ ;
COMINS, DL .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) :2656-2657
[6]   Total synthesis of clavepictines A and B. Cross-coupling of an acylenamino triflate and cyclization of a beta-aminoallene [J].
Ha, JD ;
Lee, DH ;
Cha, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4550-4551
[7]   Intramolecular [3+2] annulation of olefin-tethered cyclopropylamines [J].
Ha, JD ;
Lee, JW ;
Blackstock, SC ;
Cha, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8510-8514
[8]   Asymmetric synthesis of chiral, nonracemic trifluoromethyl-substituted piperidines and decahydroquinolines [J].
Jiang, JL ;
DeVita, RJ ;
Doss, GA ;
Goulet, MT ;
Wyvratt, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (03) :593-594
[9]   Palladium-catalysed coupling of vinyl phosphates with aryl or heteroaryl boronic acids. Application to the synthesis of substituted nitrogen containing heterocycles [J].
Lepifre, F ;
Buon, C ;
Rabot, R ;
Bouyssou, P ;
Coudert, G .
TETRAHEDRON LETTERS, 1999, 40 (35) :6373-6376
[10]   Synthesis and reactivity of pyrrolidinone- and piperidinone-derived enol triflates [J].
Luker, T ;
Hiemstra, H ;
Speckamp, WN .
TETRAHEDRON LETTERS, 1996, 37 (45) :8257-8260