Unexpected Pyridinyl Group Mediated Metal-Free Wacker-Type Oxidation en Route to Pyrido[2,1-a]isoindol-5-ium Salts

Abstract

A two-step approach to rapidly access a diverse array of pyrido[2,1-a]isoindol-5-ium salts from 2-pyridinylstyrenes through an unprecedented pyridinyl group mediated metal-free Wacker-type oxidation and an acid-mediated cyclization has been developed. As a part of the mechanistic investigation of this novel Wacker-type oxidation, the abnormal instability and reactivity of the pyrido[2,1-a]isoindole intermediates were studied through DFT calculations.

Key words

polyheterocycles - pyrido[2,1-a]isoindoles - Wacker-type oxidation - metal-free - cyclization - mechanism

Publication History

Received: 11 August 2022

Accepted after revision: 07 September 2022

Accepted Manuscript online:
07 September 2022

Article published online:
10 October 2022

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