Base effect on the palladium catalyzed α-arylation of N-benzyl-2-piperidinones

被引:20
作者
Cossy, J [1 ]
de Filippis, A [1 ]
Pardo, DG [1 ]
机构
[1] ESPCI, CNRS, Lab Chim Organ Associe, F-75231 Paris 05, France
关键词
arylations; lactams; palladium; zinc; coupling;
D O I
10.1055/s-2003-42081
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A very simple method for obtaining alpha-arylated N-benzyl-2-piperidinones in high yields is described. The use of s-BuLi as the base and Pd(dba)(2) as the catalyst are the key factors.
引用
收藏
页码:2171 / 2174
页数:4
相关论文
共 36 条
[1]  
Bolm C, 2001, ANGEW CHEM INT EDIT, V40, P3285
[2]  
BRADLEY G, 1980, EUR J MED CHEM, V15, P375
[3]   Palladium-catalyzed intermolecular α-arylation of N-protected 2-piperidinones [J].
Cossy, J ;
de Filippis, A ;
Pardo, DG .
ORGANIC LETTERS, 2003, 5 (17) :3037-3039
[4]   Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].
Culkin, DA ;
Hartwig, JF .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245
[5]   CENTRAL NERVOUS-SYSTEM ACTIVE COMPOUNDS .1. SYNTHESIS OF SOME CAPROLACTAM DERIVATIVES SUBSTITUTED AT N1, C2 AND C3 [J].
DUONG, T ;
PRAGER, RH ;
WARD, AD ;
KERR, DIB .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (12) :2651-2665
[6]   ARYLATION OF REFORMATSKY REAGENT CATALYZED BY ZEROVALENT COMPLEXES OF PALLADIUM AND NICKEL [J].
FAUVARQUE, JF ;
JUTAND, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 132 (02) :C17-C19
[7]   CATALYSIS OF THE ARYLATION OF THE REFORMATSKY REAGENT BY PALLADIUM OR NICKEL-COMPLEXES - SYNTHESIS OF ARYL ACID-ESTERS [J].
FAUVARQUE, JF ;
JUTAND, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 177 (01) :273-281
[8]  
Freund R, 2000, HELV CHIM ACTA, V83, P1247, DOI 10.1002/1522-2675(20000607)83:6<1247::AID-HLCA1247>3.0.CO
[9]  
2-1
[10]   PHOTOINDUCED CYCLIZATIONS OF MONOANIONS AND DIANIONS OF N-ACYL-ORTHO-CHLORANILINES AND N-ACYL-ORTHO-CHLOROBENZYLAMINES AS GENERAL-METHODS FOR THE SYNTHESIS OF OXINDOLES AND 1,4-DIHYDRO-3(2H)-ISOQUINOLINONES [J].
GOEHRING, RR ;
SACHDEVA, YP ;
PISIPATI, JS ;
SLEEVI, MC ;
WOLFE, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (02) :435-443