Recent Advances in the Generation of Nitrilium Betaine 1,3-Dipoles

Abstract

Nitrilium betaine 1,3-dipoles are ubiquitous reagents in organic chemistry, with applications ranging from natural product synthesis to materials science. Given the high reactivity of these zwitterionic motifs, they are invariably generated in situ from a suitable precursor, prior to use. This short review summarises the recent progress in the development of modern approaches towards the formation of these 1,3-dipoles, and their applications within a diverse range of fields.

1 Introduction

2 Nitrile Ylides

2.1 2H-Azirine Rearrangement

2.2 Addition of Nitriles to Carbenes

3 Nitrile Imines

3.1 2,5-Tetrazole Thermolysis

3.2 2,5-Tetrazole Photolysis

3.3 Diaryl Sydnone Photolysis

4 Nitrile Oxides

4.1 Hypervalent Iodine

4.2 The Nitroso Radical

4.3 Green Chemistry Approaches

4.4 Other Approaches

5 Conclusions

Key words

1,3-dipole - dipolar cycloaddition - nitrilium betaine - nitrile ylide - nitrile imine - nitrile oxide - photochemistry

Publication History

Received: 21 December 2020

Accepted after revision: 11 February 2021

Accepted Manuscript online:
11 February 2021

Article published online:
10 March 2021

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