A Single-Step Synthesis of Stereodefined Skipped Trienes: Pd-Catalyzed Cascade Reaction of Terminal Alkynes with Allylic Halides

A Pd-catalyzed cascade reaction of terminal alkynes with allylic halides for the efficient construction of stereodefined skipped trienes under mild reaction conditions in a single-step has been reported. A variety of functional groups were well tolerated within the catalytic system, providing a variety of substituted stereodefined skipped trienes in moderate to good yields. Preliminary mechanism investigations indicated that the Sonogashira reaction as the intermediate step and the radical pathway might not be involved in this novel multicomponent coupling reaction.

Automated summary

A Pd-catalyzed cascade reaction has been reported for the efficient construction of stereodefined skipped trienes under mild reaction conditions in a single-step. The reaction tolerates a variety of functional groups and provides substituted stereodefined skipped trienes in moderate to good yields. Preliminary mechanism investigations suggest that the Sonogashira reaction and radical pathway may not be involved in this novel multicomponent coupling reaction.