N-Heterocyclic carbene catalyzed tail-to-tail oligomerization of N,N-dimethylacrylamide (DMAA) and the search for the Stetter reaction of DMAA with benzaldehyde

被引：21

作者：

Rajachan, Oue-artom ^{[1
,2
]}

Paul, Mathias ^{[3
]}

Yatham, Veera Reddy ^{[3
]}

Neudoerfl, Joerg-M. ^{[3
,4
]}

Kanokmedhakul, Kwanjai ^{[1
,2
]}

Kanokmedhakul, Somdej ^{[1
,2
]}

Berkessel, Albrecht ^{[3
]}

机构：

[1] Khon Kaen Univ, Dept Chem, Nat Prod Res Unit, Khon Kaen 40002, Thailand

[2] Khon Kaen Univ, Ctr Excellence Innovat Chem, Fac Sci, Khon Kaen 40002, Thailand

[3] Univ Cologne, Dept Chem, D-50939 Cologne, Germany

[4] Univ Cologne, Xray Crystallog, D-50939 Cologne, Germany

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 47期

关键词：

N-Heterocyclic carbene; Michael acceptor; Umpolung; Tail-to-tail oligomerization; Organocatalysis; THIAMINE ACTION; UMPOLUNG; DIMERIZATION; MECHANISM; INTERMEDIATE; GENERATION;

D O I：

10.1016/j.tetlet.2015.09.104

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tail-to-tail oligomerization of N,N-dimethylacrylamide catalyzed by N-heterocyclic carbenes (NHCs) was investigated, giving the dimerization and trimerization products in a moderate combined yield. Reaction intermediates involved in the new oligomerization have been observed by NMR and ESI-MS. We showed the first NHC-catalyzed cross coupling of methyl methacrylate and N,N-dimethylaciylamide, and the reaction of benzaldehyde/benzoin with N,N-dimethylacrylamide. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：6537 / 6540

页数：4

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