Tandem Cross-Coupling of Alkynyl Sulfides and Alkynyl Sulfoxides/[3,3]-Sulfonium Rearrangement to Construct Tetrasubstituted Furans
Shuyu Meng, Yinglan Wang, Jie Liu, Jie Zheng, Xiao Qian, Quanrui Wang
Abstract
In the presence of boron trifluoride, a variety of alkynyl sulfides and alkynyl sulfoxides undergo tandem cross-coupling/[3,3]-sulfonium rearrangement followed by 5- exo -dig heterocyclization. The strategy provides concise access to novel tetrasubstituted furans in good to high yields with 100% atom-economy efficiency. Further derivatization of the resultant furans was feasible by utilizing the incorporated alkylthio groups.
Topics & Concepts
ChemistryTandemDerivatizationCascade reactionConstruct (python library)Combinatorial chemistryReaction conditionsYield (engineering)Medicinal chemistryBoronRegioselectivityOrganic chemistryStereochemistryVariety (cybernetics)Sulfur-Based Synthesis TechniquesCatalytic Alkyne ReactionsCatalytic C–H Functionalization Methods