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Synthesis 2018; 50(12): 2281-2306
DOI: 10.1055/s-0036-1591993
DOI: 10.1055/s-0036-1591993
review
An Update of N-Tosylhydrazones: Versatile Reagents for Metal-Catalyzed and Metal-Free Coupling Reactions
We are grateful for the financial support from NSFC (21672184), the Program for Changjiang Scholars and Innovative Research Team in University (IRT13095), the Program for Innovative Research Team (in Science and Technology) in University of Yunnan Province, YunLing scholar of Yunnan Province, and Yunnan University.Further Information
Publication History
Received: 04 February 2018
Accepted after revision: 06 March 2018
Publication Date:
23 May 2018 (online)
Abstract
N-Tosylhydrazones have had widespread application in organic synthesis for more than a half century. In most of cases, N-tosylhydrazones, as masked diazo compounds, have been generally used in a series of important carbon–carbon and carbon–heteroatom bond-forming reactions. This review provides an update on progress in diverse coupling reactions of N-tosylhydrazones since 2012. The examples selected are mainly categorized by metal-catalyzed and metal-free systems, wherein four main types of transformations including insertion, olefination, alkynylation, and cyclization are discussed for each system.
1 Introduction
2 Transition-Metal-Catalyzed Coupling Reactions
3 Metal-Free Coupling Reactions
4 Conclusion and Outlook
-
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For reviews on the use of N-tosylhydrazones and diazo compounds in transition-metal-catalyzed coupling reaction involving metal–carbene formation, see:
For previous reviews on the transition-metal-catalyzed and metal-free coupling reactions of N-tosylhydrazones, see:
For reviews on the synthesis of (hetero)cyclic compounds via N-tosylhydrazones, see:
For selected previous examples on Pd-catalyzed coupling reaction of N-tosylhydrazones, see:
For previous review and recent examples on the synthesis of alkenes from N-tosylhydrazones:
For recent reviews and selected examples on the photocatalytic annulation of hydrazones, see:
For C–O bond formation by esterification of hydrazones with carboxylic acids, see:
For C–S bond formation from N-tosylhydrazones, see:
For examples on the C–X bond formation via halogenation of N-tosylhydrazones, see:
For recent examples on the cyclopropanation reaction of N-tosylhydrazones toward functional fullerene derivatives, see:
For examples on the construction of indazoles via intermolecular metal-free annulation of N-tosylhydrazones, see:
For examples on the construction of indazoles via intramolecular metal-free catalyzed annulation of N-tosylhydrazones, see:
For examples on the construction of indazoles via transition-metal-catalyzed annulation of N-tosylhydrazones, see: