Divergent Reactivity of Iminyl Radicals in Four Interrupted Pathways for the Synthesis of Cyclic/Acyclic Ketones and N-Heterocycles from Vinyl Azides and Phenylacetic Acids
Swagota Paul,
Ashitosh Baruah,
Atul A. More
Abstract:Herein, we report the Ag-catalyzed substrate-controlled interrupted radical pathways of the iminyl radical. The benzylic groups played a crucial role in pathway selection involving a series of dimerization and hydrolysis, a 1,5-H shift followed by cascade radical cyclization, and direct N-(sp 2 )/aromatization reactions that provide access to diverse cyclic/acyclic ketones, quinolines, and phenanthridine derivatives. Contrary to previous reports, mechanistic investigations with high-resolution mass spectrometr… Show more
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