Nickel-Catalyzed, Directing-Group-Assisted [2+2+2] Cycloaddition of Imine and Alkynes

被引：26

作者：

Adak, Laksmikanta ^{[1
]}

Chan, Wei Chuen ^{[1
]}

Yoshikai, Naohiko ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2011年 / 6卷 / 02期

基金：

新加坡国家研究基金会;

关键词：

alkynes; cycloaddition; density functional calculations; heterocycles; nickel; BOND ACTIVATION; CARBON-DIOXIDE; ALLYLIC AMINES; C-H; METAL; 1,6-DIYNES; CONSTRUCTION; CYCLOTRIMERIZATION; REGIOSELECTIVITY; ISOTHIOCYANATES;

D O I：

10.1002/asia.201000564

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An aldimine bearing a 3-methyl-2-pyridyl group undergoes [2+2+2] cycloaddition reaction with two alkyne molecules under nickel catalysis to afford a 1,2-dihydropyridine derivative in moderate to good yield. The reaction is likely to involve oxidative cyclization of the imine and alkyne, insertion of another alkyne, and C-N reductive elimination, followed by a 1,5-sigmatropic hydrogen shift. The pyridyl group is proposed to facilitate the reaction by chelation to the aza-nickelacycle intermediates. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：359 / 362

页数：4

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