Recent Advances in Transition-Metal-Catalyzed Denitrogenative Transformations­ of 1,2,3-Triazoles and Related Compounds

Abstract

Suitably substituted electron-deficient 1,2,3-triazoles exist in equilibrium with their ring-opened α-diazoimine tautomers. This phenomenon was used to facilitate the generation of synthetically useful metallo azavinyl carbene intermediates. In this short review, we describe recent developments in the transition-metal-catalyzed decomposition of electron-deficient (annulated) 1,2,3-triazoles to form metallo azavinyl carbenes, and their application in the synthesis of highly functionalized nitrogen-based heterocycles and building blocks through various synthetic transformations, such as transannulation, cyclopropanations, insertion reactions, ylide formation/rearrangements, and ring expansions.

1 Introduction

2 Ring–Chain Isomerism

3 Synthesis of N-Sulfonyl-1,2,3-triazoles

4 Denitrogenative Transformations of 1,2,3-Triazoles

4.1 Transannulations with Nitriles and Alkynes

4.2 Transannulations with Alkenes or Carbonyl Compounds

4.3 Transannulations with (Hetero)cumulenes or 1,3-Dienes

4.4 Insertions into X–H or C–X bonds

4.5 Rearrangement/Ring Expansion

4.6 Miscellaneous Transformations

5 Summary and Outlook

Key words

triazoles - carbenes - imines - diazo compounds - catalysis - rhodium

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