[2+3] Annulative Coupling of Tetrahydroisoquinolines with Aryliodonio diazo compounds To Access 1,2,4-Triazolo[3,4-a]isoquinolines

Base promoted one-pot annulative coupling of 1,2,3,4-tetrahydroisoquinolines (THIQs) with hypervalent iodine(III) species aryliodonio diazo compounds has been devised for the direct construction of 1,2,4-triazolo[3,4-a]isoquinoline derivatives at room temperature in open air for the first time. This approach involves [2 + 3] cascade annulation of nucleophilic THIQ with an electrophilic aryliodonio diazo compound via N-H and alpha-C1(sp3)-H difunction-alization of THIQ.

Automated summary

A one-pot annulative coupling reaction of 1,2,3,4-tetrahydroisoquinolines (THIQs) with hypervalent iodine(III) species aryliodonio diazo compounds has been developed, leading to the direct construction of 1,2,4-triazolo[3,4-a]isoquinoline derivatives at room temperature in open air. This reaction involves a [2 + 3] cascade annulation of nucleophilic THIQ with an electrophilic aryliodonio diazo compound, enabling the N-H and alpha-C1(sp3)-H difunctionalization of THIQ.