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在无特定螯合体系的情况下，镍催化芳族酰胺与炔烃的C-H/N-H环化反应。

Nickel-catalyzed C-H/N-H annulation of aromatic amides with alkynes in the absence of a specific chelation system.

作者信息

Obata Atsushi, Ano Yusuke, Chatani Naoto

机构信息

Department of Applied Chemistry , Faculty of Engineering , Osaka University , Suita , Osaka 565-0871 , Japan.

出版信息

Chem Sci. 2017 Sep 1;8(9):6650-6655. doi: 10.1039/c7sc01750b. Epub 2017 Jul 24.

DOI:10.1039/c7sc01750b
PMID:28989692
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5625264/
Abstract

The Ni-catalyzed reaction of aromatic amides with alkynes in the presence of KOBu involves C-H/N-H oxidative annulation to give 1(2)-isoquinolinones. A key to the success of the reaction is the use of a catalytic amount of strong base, such as KOBu . The reaction shows a high functional group compatibility. The reaction with unsymmetrical alkynes, such as 1-arylalkynes, gives the corresponding 1(2)-isoquinolinones with a high level of regioselectivity. This discovery would lead to the development of Ni-catalyzed chelation-assisted C-H functionalization reactions without the need for a specific chelation system.

摘要

在叔丁醇钾存在下，镍催化芳族酰胺与炔烃反应，通过C-H/N-H氧化环化生成1(2)-异喹啉酮。该反应成功的关键在于使用催化量的强碱，如叔丁醇钾。该反应显示出高官能团兼容性。与不对称炔烃（如1-芳基炔烃）反应，能以高区域选择性得到相应的1(2)-异喹啉酮。这一发现将推动无需特定螯合体系的镍催化螯合辅助C-H官能化反应的发展。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0ec/5625264/1851d9ba0a68/c7sc01750b-s9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0ec/5625264/660538ff8d71/c7sc01750b-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0ec/5625264/1851d9ba0a68/c7sc01750b-s9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0ec/5625264/660538ff8d71/c7sc01750b-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0ec/5625264/1851d9ba0a68/c7sc01750b-s9.jpg

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