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DOI: 10.1055/s-0040-1719930
Recent Advances in Transition-Metal-Catalyzed Reactions of N-Tosylhydrazones
Abstract
N-Tosylhydrazones are highly versatile precursors for in situ carbene formation and are frequently used in metal-catalyzed cross-coupling reactions. Due to their many applications in organic synthesis, including C–C, C–O, C–N, and C–S bond formation, N-tosylhydrazones have recently received much interest. They can be simply synthesized by reacting an aldehyde or ketone with N-tosylhydrazine to produce a solid N-tosylhydrazone, which is a ‘green’ precursor of diazo compounds. Using a suitable metal catalyst, N-tosylhydrazones show versatile substrate scope for the synthesis of substituted diaminopyrroles, chromenopyrazoles, alkenylpyrazoles, benzofuran thioethers, tetrahydropyridazines, sulfur-containing heterocycles, and benzofurans with potent biological activities and even regioselective N-functionalization reactions. Metal-catalyzed reactions of N-tosylhydrazones for the construction of bioactive heterocycles are still highly in demand. Hence, this review focuses on the recent synthetic application of N-tosylhydrazones influenced by different transition metals with notable features like simple workup procedures, gram-scale synthesis, broad substrate scope, multicomponent processes, cyclization, and carbon–heteroatom bond formation.
1 Introduction
2 Applications of N-Tosylhydrazones
3 Conclusion
Key words
N-tosylhydrazone - cross-coupling reaction - regioselective - carbene - cycloaddition - olefinationPublikationsverlauf
Eingereicht: 15. April 2022
Angenommen: 26. April 2022
Artikel online veröffentlicht:
30. Juni 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
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