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Efficient Access to Isoquinolines via Rhodium-Catalyzed Oxidative Annulation of Pyridyl C–H Bonds Directed by Carbonyl with Internal Alkynes
Synthesis ( IF 2.2 ) Pub Date : 2020-09-15 , DOI: 10.1055/s-0040-1707387
Fuwei Li 1 , Lijun Shi 1, 2 , Mingshan Wen 1
Affiliation  


Abstract

An efficient synthesis of amino-substituted isoquinolines via Rh(III)-catalyzed oxidative [2+2+2] annulation of pyridines with alkynes has been developed, which is cooperatively enabled by a directing carbonyl and steric hindrance adjacent to the amino group of the pyridine, via a six-membered rhodacyclic intermediate without coordination with the pyridinic nitrogen. The establishment of this C–H activation strategy also paves the way for other oxidative transformations of heterocyclic C–H bonds.



Publication History

Received: 20 July 2020

Accepted after revision: 18 August 2020

Publication Date:
15 September 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany



中文翻译:

通过铑催化羰基与内部炔烃键合的吡啶基CH键的环化反应,可高效获得异喹啉


摘要

已开发了通过Rh(III)催化的吡啶与炔烃的氧化[2 + 2 + 2]环合反应,有效合成氨基取代的异喹啉的方法,这是通过直接与碳原子的氨基相邻的羰基和空间位阻进行的吡啶,通过六元的Rhodocyclic中间体,不与吡啶氮进行配位。这种C–H活化策略的建立也为杂环C–H键的其他氧化转化铺平了道路。



出版历史

收到:2020年7月20日

修订后接受:2020年8月18日

发布日期:
2020年9月15日(在线)

©2020年。Thieme。版权所有

Georg Thieme Verlag
KGRüdigerstraße14,70469斯图加特,德国

更新日期:2020-09-16
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