Silver carbenoids derived from diazo compounds: A historical perspective on challenges and opportunities

Transition-metal-catalyzed transfer of a carbene group from diazo compounds has great significance in the field of organic synthesis by allowing access to valuable chemicals from structurally simple compounds. Silver catalysts have recently been recognized as a powerful alternative to other transition-metal catalysts (e.g., Cu, Rh, and Au) because of their low cost and unique reactivity profiles, and they can also drastically enhance the rate and selectivity of the reaction, as well as suppress the competitive dimerization process. This review highlights the tunable homogeneous silver-catalyzed carbene transfer reactions and emphasizes their specificities over other transition-metal catalysts. The discussion is primarily organized on the basis of the different reactions catalyzed by Ag(I) salts or complexes that diazo compounds can undergo, and their applications in total synthesis are treated in specific subsections. The detailed mechanisms of selected reactions and the remaining challenges and drawbacks are highlighted for the design of new silver catalysts.

Automated summary

This review article discusses the importance of transition-metal-catalyzed carbene transfer reactions in organic synthesis, with a focus on the advantages and specificities of silver catalysts over other transition metals. The specific reactions catalyzed by Ag(I) salts or complexes and their applications in total synthesis are highlighted, along with the detailed mechanisms and remaining challenges for the design of new silver catalysts.