Synlett 2015; 26(16): 2189-2193
DOI: 10.1055/s-0034-1381186
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© Georg Thieme Verlag Stuttgart · New York

Azomethine Ylide: An Isolable 1,5-Dipole for Affecting [5+2] Cy­cloaddition Reactions

Eun Jeong Yoo*
Department of Chemistry, Kangwon National University, Chuncheon, 200-701, Republic of Korea   Email: ejyoo@kangwon.ac.kr
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Further Information

Publication History

Received: 29 April 2015

Accepted after revision: 12 June 2015

Publication Date:
22 July 2015 (online)


Abstract

It was recently found that 1-sulfonyl-1,2,3-triazole can act as a 1,3-dipole in the presence of rhodium(II), leading to emergence of diverse rhodium(II)-catalyzed [3+n] cycloaddition reactions using 1-sulfonyl-1,2,3-triazole. Herein, we highlight development of another dipole, azomethine ylide, which was prepared from 1-sulfonyl-1,2,3-triazole with amide and pyridine derivatives, respectively. Notably, the rhodium(II)-catalyzed reaction of 1-sulfonyl-1,2,3-triazole with pyridines resulted in generation of uniquely isolable azomethine ylide. This azomethine ylide is the first example of an isolable 1,5-dipole that could be cyclized with 2π-dipolarophiles. The new 1,5-dipole provides an avenue for the development of new organic syntheses.

1 Introduction

2 Reactions of 1-Sulfonyl-1,2,3-triazole with Aldehyde

3 1-Sulfonyl-1,2,3-triazole as a Precursor of Azomethine Ylide

4 Generation of Free Azomethine Ylide

5 Outlook

 
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