Construction of pyrroles, furans and thiophenes <i>via</i> intramolecular cascade desulfonylative/dehydrogenative cyclization of vinylidenecyclopropanes induced by NXS (X = I or Br)
Zhe Meng, Jun Yan, Chao Ning, Min Shi, Yin Wei
Abstract
NXS mediated desulfonylative/dehydrogenative cyclization of vinylidenecyclopropanes (VDCPs). The advantages of this method include wide substrate range, high efficiency and synthetic usefulness of the heterocyclic products under metal-free and mild conditions. The derivatization of pyrrole products and the preparation of functional molecules successfully demonstrated the synthetic potential of the products as platform molecules. The reaction mechanism has been investigated on the basis of control experiments and DFT calculations.
Topics & Concepts
Intramolecular forceCascadeChemistryMedicinal chemistryCombinatorial chemistryStereochemistryChromatographyCyclopropane Reaction MechanismsSulfur-Based Synthesis TechniquesCatalytic Alkyne Reactions