One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation

Herein, we report an efficient method for the synthesis of (Z)-beta-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction promoted by palladium-copper catalyst and Bronsted acid. The ynone intermediates are generated in situ from readily available acid chlorides and terminal alkynes at room temperature, which are directly converted to (Z)-beta-halovinyl ketones by treating with triflic acid. This method avoids the use of an external halogen source and features broad substrate scope, high yield, and good to excellent stereoselectivity.

Automated summary

This method involves the synthesis of (Z)-beta-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction using a palladium-copper catalyst and Bronsted acid. It allows for the direct conversion of ynone intermediates to the desired product without the need for an external halogen source, resulting in high yields and good to excellent stereoselectivity.