Efficient Access to Isoquinolines via Rhodium-Catalyzed Oxidative Annulation of Pyridyl C–H Bonds Directed by Carbonyl with Internal Alkynes,Synthesis

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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.