Synthesis, Table of Contents Synthesis 2022; 54(24): 5434-5444DOI: 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 Dong Shi , Tao Zeng , Xin Lei , Xiaotong Wu , Mansirun Li , Yandong Zhang∗ Recommend Article Abstract Buy Article All articles of this category 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 Key wordspolyheterocycles - pyrido[2,1-a]isoindoles - Wacker-type oxidation - metal-free - cyclization - mechanism Full Text References References 1a Mitsumori T, Bendikov M, Dautel O, Wudl F, Shioya T, Sato H, Sato Y. J. Am. Chem. Soc. 2004; 126: 16793 1b Badaro JS. A, Koszarna B, Bousquet MH. E, Ouellette ET, Jacquemin D, Gryko DT. Org. Chem. Front. 2022; 9: 1861 2a Vlahovici A, Druţă I, Andrei M, Cotlet M, Dinică R. J. Lumin. 1999; 82: 155 2b Vlahovici A, Andrei M, Druţă I. J. Lumin. 2002; 96: 279 3a Ambros R, von Angerer S, Wiegrebe W. Arch. Pharm. (Weinheim, Ger.) 1988; 321: 481 3b Orlemans EO. M, Verboom W, Scheltinga MW, Reinhoudt DN, Lelieveld P, Fiebig HH, Winterhalter BR, Double JA, Bibby MC. J. Med. Chem. 1989; 32: 1612 3c Wang S, Cao L, Shi H, Dong Y, Sun J, Hu Y. Chem. Pharm. Bull. 2005; 53: 67 3d Martínez-Viturro CM, Domínguez D. Tetrahedron Lett. 2007; 48: 4707 3e Lubbers T, Angehrn P, Gmunder H, Herzig S. Bioorg. Med. Chem. 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