Modular synthesis and transition metal-free alkynylation/alkenylation of Castagnoli–Cushmanderived N,O- and N,S-heterocyclic vinyl chlorides

Authors

Timothy K. Beng, Central Washington UniversityFollow
Abdikani Omar Farah, Central Washington University
Victoria Shearer, Central Washington University

Document Type

Article

Department or Administrative Unit

Chemistry

Publication Date

10-7-2020

Abstract

A modular and functional group-tolerant protocol for the transition metal-free coupling of novel N,O- and N,S-heterocyclic vinyl chlorides with terminal acetylenes and styrenes has been developed, leading to the epimerization-free synthesis of fully carbofunctionalized dihydro-1,4-oxazines/thiazines. Bicyclic morpholines have also been prepared through the interrogation of newly synthesized cross-conjugated dienes in Diels–Alder reactions. The use of environmentally benign reaction media endows the current strategy with a practical advantage.

Comments

This article was originally published Open Access in RSC Advances. The full-text article from the publisher can be found here.

Recommended Citation

Beng, T. K., Farah, A. O., & Shearer, V. (2020). Modular synthesis and transition metal-free alkynylation/alkenylation of Castagnoli–Cushman-derived N,O- and N,S-heterocyclic vinyl chlorides. RSC Advances, 10(61), 37153–37160. https://doi.org/10.1039/d0ra06619b

Journal

RSC Advances

Creative Commons License

This work is licensed under a Creative Commons Attribution-Noncommercial 3.0 License

Rights

This journal is © The Royal Society of Chemistry 2020