Synthesis of Terminal Allenes through Copper-Mediated Cross-Coupling of Ethyne with <i>N</i>-Tosylhydrazones or α-Diazoesters

Abstract

Ethyne is employed as coupling partner in copper-mediated cross-coupling reactions with N-tosylhydrazones and α-diazoacetate, leading to the development of a new synthetic method for terminal allenes. With this novel coupling method, the terminal allenes were obtained in good yields and with excellent functional group tolerance. Copper carbene migratory insertion is proposed as the key step in these transformations.