Procedures for and possible mechanisms of Pd-catalyzed allylations of primary and secondary amines with allylic alcohols

被引:165
作者
Muzart, Jacques [1 ]
机构
[1] Univ Reims, CNRS, Unit Mix Rech, F-51687 Reims, France
关键词
allylic alcohol; allylic amine; allylation; palladium; promoter; reaction mechanisms; DIPHOSPHINIDENECYCLOBUTENE-COORDINATED PALLADIUM; PALLADIUM(0)-CATALYZED ALLYLATION; (PI-ALLYL)PALLADIUM COMPLEXES; TANDEM ALLYLATION; 3-STEP SYNTHESIS; C-O; ANILINES; AMINATION; ACID; ALKYLATION;
D O I
10.1002/ejoc.200601050
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This review describes the different Pd-catalyzed methods that afford allylic amines from intermolecular reactions between allylic alcohols and amines and, with personal comments, the mechanisms that have been proposed. Allylic amines are an important class of compounds, while a wide structural variety of allylic alcohols are commercially available and are abundant in nature. The advantages of the use of allylic alcohols over that of their derivatives such as allylic esters or carbonates are the high atom efficiency and the formation only of water as the by-product.
引用
收藏
页码:3077 / 3089
页数:13
相关论文
共 77 条
[1]   AMINATION OF PI-ALLYLPALLADIUM CHLORIDE COMPLEXES - A MECHANISTIC STUDY [J].
AKERMARK, B ;
AKERMARK, G ;
HEGEDUS, LS ;
ZETTERBERG, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3037-3040
[2]   EVIDENCE OF THE FORMATION OF ZEROVALENT PALLADIUM FROM PD(OAC)2 AND TRIPHENYLPHOSPHINE [J].
AMATORE, C ;
JUTAND, A ;
MBARKI, MA .
ORGANOMETALLICS, 1992, 11 (09) :3009-3013
[3]  
ATKINS KE, 1970, TETRAHEDRON LETT, P3821
[4]  
BACKVALL JE, 1991, ISRAEL J CHEM, V31, P17
[5]  
BACKVALL JE, 1981, J ORG CHEM, V46, P3479
[6]   PALLADIUM POLYSTYRENE CATALYSTS [J].
BERGBREITER, DE ;
CHEN, BS ;
LYNCH, TJ .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23) :4179-4186
[7]   Palladium-catalysed asymmetric allylic substitution: Synthesis of alpha- and beta-amino acids [J].
Bower, JF ;
Jumnah, R ;
Williams, AC ;
Williams, JMJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (09) :1411-1420
[8]   Nickel vs. palladium catalysts for coupling reactions of allyl alcohol with soft nucleophiles: activities and deactivation processes [J].
Bricout, H ;
Carpentier, JF ;
Mortreux, A .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 136 (03) :243-251
[9]   ASYMMETRIC SYNTHESES OF OPTICALLY-ACTIVE ALPHA,BETA-DISUBSTITUTED BETA-AMINO ACIDS [J].
BURGESS, K ;
LIU, LT ;
PAL, B .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4758-4763
[10]   Asymmetric [2+2] cycloaddition: Total synthesis of (-)-swainsonine and (+)-6-epicastanospermine [J].
Ceccon, Julien ;
Greene, Andrew E. ;
Poisson, Jean-Francois .
ORGANIC LETTERS, 2006, 8 (21) :4739-4742