Unusual regioselectivity in Pd(0)-catalyzed coupling of allylic monoacetates and nitroalkanes: one-pot isomerization-alkylation

被引:1
作者
Khan, Pasha M. [1 ]
Bisht, Kirpal S. [1 ]
机构
[1] Univ S Florida, Dept Chem, Tampa, FL 33620 USA
关键词
(PI-ALLYL)PALLADIUM COMPLEXES; CATALYZED REACTION; ALLYLATION; NITRO; SUBSTITUTIONS; CONVERSION; MECHANISM; ATTACK;
D O I
10.1016/j.tetlet.2010.01.025
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A hitherto unknown palladium-catalyzed reaction of nitroalkanes with hydroxy allylic acetates is reported. The reaction led to the formation of gamma-nitrocarbonyl Compounds instead of the usual unsaturated nitroalcohol expected upon displacement of the allylic acetate group. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1407 / 1410
页数:4
相关论文
共 48 条
[1]   PALLADIUM CATALYZED C-ALLYLATION OF NITROALKANES [J].
ALEKSANDROWICZ, P ;
PIOTROWSKA, H ;
SAS, W .
TETRAHEDRON, 1982, 38 (09) :1321-1327
[2]   PALLADIUM CATALYZED ALLYLATION OF NITROALKANES WITH ALLYL CHLORIDES [J].
ALEKSANDROWICZ, P ;
PIOTROWSKA, H ;
SAS, W .
MONATSHEFTE FUR CHEMIE, 1982, 113 (10) :1221-1224
[3]  
[Anonymous], 1994, The Organic Chemistry of Aliphatic Nitrogen Compounds
[4]  
[Anonymous], 2008, ORGANOMETALLICS
[5]   Central versus terminal attack in nucleophilic addition to (pi-allyl)palladium complexes. Ligand effects and mechanism [J].
Aranyos, A ;
Szabo, KJ ;
Castano, AM ;
Backvall, JE .
ORGANOMETALLICS, 1997, 16 (05) :1058-1064
[6]   Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction) [J].
Ballini, R ;
Petrini, M .
TETRAHEDRON, 2004, 60 (05) :1017-1047
[7]   CONJUGATED NITROALKENES - VERSATILE INTERMEDIATES IN ORGANIC-SYNTHESIS [J].
BARRETT, AGM ;
GRABOSKI, GG .
CHEMICAL REVIEWS, 1986, 86 (05) :751-762
[8]  
Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
[9]  
Brunel JM, 2001, EUR J ORG CHEM, V2001, P1009, DOI 10.1002/1099-0690(200103)2001:5<1009::AID-EJOC1009>3.0.CO
[10]  
2-3