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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.
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
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