Direct Access to α,β-Alkynylamides via Pd-Catalyzed Carbonylation of Terminal Alkynes with Amines Using Chloroform as the CO Surrogate

Wedescribe the first-time use of a palladium-di-(1-adamantyl)-n-butylphosphine catalytic system for the synthesis of alk-2-ynamidesfrom terminal alkynes via aminocarbonylation reaction. This methodavoids the direct use of toxic CO gas by utilizing chloroform as anin situ CO source. The aminocarbonylation of both aromatic and aliphaticelectron-rich alkyne nucleophiles is reported for the first time.The mild condition provides alk-2-ynamides within 50 min under microwaveirradiation at 80 degrees C.

Automated summary

We report the first-time use of a palladium-di-(1-adamantyl)-n-butylphosphine catalytic system for the synthesis of alk-2-ynamides via aminocarbonylation reaction. This method utilizes chloroform as an in situ CO source, avoiding the direct use of toxic CO gas. The mild condition provides alk-2-ynamides within 50 min under microwave irradiation at 80 degrees C.