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Synthesis 2022; 54(24): 5434-5444
DOI: 10.1055/a-1938-2521
DOI: 10.1055/a-1938-2521
feature
Unexpected Pyridinyl Group Mediated Metal-Free Wacker-Type Oxidation en Route to Pyrido[2,1-a]isoindol-5-ium Salts
Financial support from the National Natural Science Foundation of China (Nos. 22071205, 21772164, and 21572187), the National Fund for Fostering Talents of Basic Science (NFFTBS, J1310024), and the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT) is acknowledged.
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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 - mechanismSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1938-2521.
- Supporting Information
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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