Efficient coupling reactions of allylamines with soft nucleophiles using nickel-based catalysts

被引：29

作者：

Bricout, H ^{[1
]}

Carpentier, JF ^{[1
]}

Mortreux, A ^{[1
]}

机构：

[1] ENSCL,GRP CHIM ORGAN APPL,URA CNRS 402,CATALYSE HETEROGENE & HOMOGENE LAB,F-59652 VILLENEUVE DASCQ,FRANCE

来源：

CHEMICAL COMMUNICATIONS | 1997年 / 15期

关键词：

D O I：

10.1039/a702954c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Substitution reactions of N,N-diethylallylamine 1 with soft nucleophiles such as active methylene compounds 2a-c and piperidine 5 proceed much more rapidly in the presence of Ni(dppb)(2) [dppb = 1,4-bis(diphenylphosphino)butane] as catalyst than with comparable palladium systems.

引用

收藏

页码：1393 / 1394

页数：2

相关论文

共 12 条

[1]

ATKINS KE, 1970, TETRAHEDRON LETT, V43, P3821

[2] Further developments in metal-catalysed C-C bond cleavage in allylic dimethyl malonate derivatives [J].

Bricout, H ;

Carpentier, JF ;

Mortreux, A .

TETRAHEDRON LETTERS, 1997, 38 (06) :1053-1056

[3] NICKEL-CATALYZED SUBSTITUTION-REACTIONS OF ALLYLIC COMPOUNDS WITH SOFT NUCLEOPHILES - AN EFFICIENT ALTERNATIVE TO PALLADIUM CATALYSIS [J].

BRICOUT, H ;

CARPENTIER, JF ;

MORTREUX, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (18) :1863-1864

[4] MILD AND SELECTIVE PALLADIUM(0)-CATALYZED DEALLYLATION OF ALLYLIC AMINES - ALLYLAMINE AND DIALLYLAMINE AS VERY CONVENIENT AMMONIA EQUIVALENTS FOR THE SYNTHESIS OF PRIMARY AMINES [J].

GARROHELION, F ;

MERZOUK, A ;

GUIBE, F .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :6109-6113

[5] PD CATALYZED INTRAMOLECULAR COUPLING BETWEEN TERTIARY-AMINES AND ALLYLIC GROUPS - SYNTHESIS OF 3-HYDRO-1H-2-BENZAZEPINIUM SALTS [J].

GRELLIER, M ;

PFEFFER, M ;

VANKOTEN, G .

TETRAHEDRON LETTERS, 1994, 35 (18) :2877-2880

[6] 2-DIMETHYLAMINOMETHYL-3-TRIMETHYLSILYLMETHYLBUTA-1,3-DIENE AS A SYNTHETIC EQUIVALENT OF 2,2'-BIALLYL ZWITTERIONIC SPECIES [J].

HOSOMI, A ;

HOASHI, K ;

KOHRA, S ;

TOMINAGA, Y ;

OTAKA, K ;

SAKURAI, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (08) :570-571

[7]

LemaireAudoire S, 1995, B SOC CHIM FR, V132, P1157

[8]

LEMAIREAUDOIRE S, 1995, TETRAHEDRON LETT, V36, P1267, DOI 10.1016/0040-4039(95)00003-U

[9] PALLADIUM-CATALYZED CARBONYLATION OF ALLYLAMINES - SYNTHESIS OF BETA,GAMMA-UNSATURATED AMIDES BY ONE-CARBON HOMOLOGATION OF ALLYLAMINES [J].

MURAHASHI, SI ;

IMADA, Y ;

NISHIMURA, K .

TETRAHEDRON, 1994, 50 (02) :453-464

[10] EXAMPLE OF THERMODYNAMIC CONTROL IN PALLADIUM-CATALYZED ALLYLIC ALKYLATION - EVIDENCE FOR PALLADIUM-ASSISTED ALLYLIC C-C BOND-CLEAVAGE [J].

NILSSON, YIM ;

ANDERSSON, PG ;

BACKVALL, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :6609-6613