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Modular Pyridine Synthesis from Oximes and Enals through Synergistic Copper/Iminium Catalysis

Ye Wei and Naohiko Yoshikai*

*Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore, Email: nyoshikaintu.edu.sg

Y. Wei, N. Yoshikai, J. Am. Chem. Soc., 2013, 135, 3756-3759.

DOI: 10.1021/ja312346s (free Supporting Information)


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Abstract

A redox-neutral, [3+3]-type condensation of O-acetyl ketoximes and α,β-unsaturated aldehydes, that is synergistically catalyzed by a copper(I) salt and a secondary ammonium salt (or amine), allows modular synthesis of a variety of substituted pyridines under mild conditions with tolerance of a broad range of functional groups. The reaction is driven by a merger of iminium catalysis and redox activity of the copper catalyst.


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Key Words

pyridines


ID: J48-Y2013-0640