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Synthesis 2014; 46(22): 3004-3023
DOI: 10.1055/s-0034-1379303
DOI: 10.1055/s-0034-1379303
short review
Recent Advances in Transition-Metal-Catalyzed Denitrogenative Transformations of 1,2,3-Triazoles and Related Compounds
Further Information
Publication History
Received: 30 August 2014
Accepted: 22 September 2014
Publication Date:
23 October 2014 (online)
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
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