Tosylhydrazones: New Uses for Classic Reagents in Palladium‐Catalyzed Cross‐Coupling and Metal‐Free Reactions

2011/07/11 by José Barluenga, Carlos Valdés · 2 citations
Chemistry · #Catalytic Cross-Coupling Reactions #Catalytic C–H Functionalization Methods #Cyclopropane Reaction Mechanisms

paper · doi:10.1002/anie.201007961

openalex publication_date 2011/07/11 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/29

Abstract

Tosylhydrazones are useful synthetic intermediates that have been used in organic chemistry for almost 60 years. The recent discovery of a palladium-catalyzed cross-coupling reaction involving a tosylhydrazone coupling partner has triggered renewed interest in these reagents. This reaction shows nearly universal generality with regard to the hydrazone and can be employed for the preparation of polysubstituted alkenes. In the course of this research, novel metal-free C-C and C-O bond-forming reactions have been discovered. Since tosylhydrazones are readily prepared from carbonyl compounds, these transformations offer new synthetic opportunities for the unconventional modification of carbonyl compounds. This Minireview discusses all of these new reactions of a classic reagent.

Citations

• A New Protocol for the In Situ Generation of Aromatic, Heteroaromatic, and Unsaturated Diazo Compounds and Its Application in Catalytic and Asymmetric Epoxidation of Carbonyl Compounds. Extensive Studies To Map Out Scope and Limitations, and Rationalization of Diastereo- and Enantioselectivities
• The Use of Tosylhydrazone Salts as a Safe Alternative for Handling Diazo Compounds and Their Applications in Organic Synthesis

Cited by

• Bridging terpenyl aldehydes and terpenes with hydrazine
• Tosylhydrazone [wikipedia]