New Application of N-Halosuccinimide/PPh₃ for the Halogenation of Propargyl Alcohols to Haloallenes

Abstract

An efficient and convenient new method has been developed for the preparation of haloallenes from propargyl alcohols by a reagent combination of N-halosuccinimide and triphenylphosphine. Chloroallenes 2 and bromoallenes 3 were obtained exclusively in moderate to good yields with regioselectivity.

Keywords:

• Haloallene
• N-halosuccinimide
• preparation
• propargyl alcohol
• triphenylphisphine

ACKNOWLEDGMENTS

We are grateful to the National Natural Science Foundation of China (20572010) for financial support. This work was partly supported by the Program for Changjiang Scholars and Innovative Research Teams in Universities (IRT0711).

Notes

^a All products are unknown compounds and were characterized by IR, ¹H and ¹³C NMR, and HRMS.

^b Isolated yields.

^a All products are unknown compounds and were characterized by IR, ¹H and ¹³C NMR, and HRMS.

^b Isolated yields.