Chelation-Assisted Nickel-Catalyzed Oxidative Annulation via Double C-H Activation/Alkyne Insertion Reaction

被引：66

作者：

Castro, Luis C. Misal ^{[1
]}

Obata, Atsushi ^{[1
]}

Aihara, Yoshinori ^{[1
]}

Chatani, Naoto ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 04期

基金：

日本科学技术振兴机构;

关键词：

alkynes; aromatic homologation; C-H activation; chelate-assistance; nickel; BOND ACTIVATION; INTERNAL ALKYNES; SUBSTITUTED NAPHTHALENES; EFFICIENT SYNTHESIS; DIRECTING GROUPS; AROMATIC AMIDES; FUNCTIONALIZATION; CLEAVAGE; ETHERS; ARENES;

D O I：

10.1002/chem.201504596

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A nickel/NHC system for regioselective oxidative annulation by double C-H bond activation and concomitant alkyne insertion is described. The catalytic reaction requires a bidentate directing group, such as an 8-aminoquinoline, embedded in the substrate. Various 5,6,7,8-tetrasubstituted-N-(quinolin-8-yl)-1-naphthamides can be prepared as well as phenanthrene and benzo[h]quinoline amide derivatives. Diarylalkynes, dialkylalkynes, and arylalkylalkynes can be used in the system. A Ni-0/Ni-II catalytic cycle is proposed as the main catalytic cycle. The alkyne plays a double role as a two-component coupling partner and as a hydrogen acceptor.

引用

页码：1362 / 1367

页数：6

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