Reassembly and functionalization of N-CF3 pyridinium salts: synthesis of nicotinaldehydes

Xiaowei Liu; Shuang Wang; Chi Gao; Wei Guan; Mang Wang

doi:10.1039/D2QO00242F

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Reassembly and functionalization of N-CF₃ pyridinium salts: synthesis of nicotinaldehydes†

Xiaowei Liu,

‡^a Shuang Wang,

‡^b Chi Gao,^a Wei Guan

*^b and Mang Wang*^a

Author affiliations

* Corresponding authors

^a Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, College of Chemistry, Northeast Normal University, Changchun 130024, China
E-mail: wangm452@nenu.edu.cn

^b Institute of Functional of Material, College of Chemistry, Northeast Normal University, Changchun, China

Abstract

Reassembly and functionalization of N-CF₃ pyridinium salts are reported. The cascade is initiated by hydrolytic ring-opening of N-CF₃ pyridinium salts, followed by defluorination, intramolecular nucleophilic addition, intermolecular nucleophilic substitution, and dehydrofluorination. The reaction exhibits tolerance to various O/N/S nucleophiles and provides a novel and efficient method for the construction of 2-functionalized nicotinaldehydes.

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Article information

DOI: https://doi.org/10.1039/D2QO00242F
Article type: Research Article
Submitted: 13 Feb 2022
Accepted: 06 Jul 2022
First published: 09 Jul 2022

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Org. Chem. Front., 2022,9, 4549-4553

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Reassembly and functionalization of N-CF₃ pyridinium salts: synthesis of nicotinaldehydes

X. Liu, S. Wang, C. Gao, W. Guan and M. Wang, Org. Chem. Front., 2022, 9, 4549 DOI: 10.1039/D2QO00242F

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