Palladium-catalyzed conversion of benzylic and allylic halides into α-aryl and β,γ-unsaturated tertiary amides by the use of a carbamoylsilane

被引:63
作者
Cunico, RF [1 ]
Pandey, RK [1 ]
机构
[1] No Illinois Univ, Dept Chem & Biochem, De Kalb, IL 60115 USA
关键词
D O I
10.1021/jo0512406
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHIC] Treatment of allylic and benzylic halides with N,N-dimethylcarbamoyl(trimethyl)silane in the presence of tetrakis(triphenylphosphine)palladium(0) affords tertiary amides, which arise from the replacement of the halogen by the N,N-dimethylcarbamoyl group.
引用
收藏
页码:9048 / 9050
页数:3
相关论文
共 18 条
[1]   Addition of carbamoylsilanes to electrophilically substituted alkenes.: Preparation of β-functionalized tertiary amides [J].
Cunico, RF ;
Motta, AR .
ORGANIC LETTERS, 2005, 7 (05) :771-774
[2]   Direct carbamoylation of alkenyl halides [J].
Cunico, RF ;
Maity, BC .
ORGANIC LETTERS, 2003, 5 (26) :4947-4949
[3]   On the preparation of carbamoylsilanes [J].
Cunico, RF ;
Chen, JX .
SYNTHETIC COMMUNICATIONS, 2003, 33 (11) :1963-1968
[4]   Direct carbamoylation of aryl halides [J].
Cunico, RF ;
Maity, MC .
ORGANIC LETTERS, 2002, 4 (24) :4357-4359
[5]   CARBONYLATION OF ALLYLIC CHLORIDES [J].
DENT, WT ;
WHITFIELD, GH ;
LONG, R .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (MAY) :1588-&
[6]   METALLIC NICKEL-MEDIATED SYNTHESIS OF KETONES BY THE REACTION OF BENZYLIC, ALLYLIC, VINYLIC, AND PENTAFLUOROPHENYL HALIDES WITH ACID HALIDES [J].
INABA, S ;
RIEKE, RD .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1373-1381
[7]   Preparation of tertiary amides from carbamoyl chlorides and organocuprates [J].
Lemoucheux, L ;
Seitz, T ;
Rouden, J ;
Lasne, MC .
ORGANIC LETTERS, 2004, 6 (21) :3703-3706
[8]   Studies relevant to palladium-catalyzed carbonylation processes. Mechanisms of formation of esters and amides from benzylpalladium and (Phenylacetyl)palladium complexes on reactions with alcohols and amines [J].
Lin, YS ;
Yamamoto, A .
ORGANOMETALLICS, 1998, 17 (16) :3466-3478
[9]   Palladium-catalyzed stereoselective synthesis of (E)-β,γ-unsaturated amides [J].
Luo, FT ;
Lu, TY ;
Xue, CH .
TETRAHEDRON LETTERS, 2003, 44 (39) :7249-7251
[10]  
MANDAI T, 2002, HDB ORGANOPALLADIUM