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Copper-Mediated Deconstructive Ring Cleavage of Cyclic Thioethers with Boron Compounds

Guanyu Wang, Dongchang Han, Yue Li, Yangleiyu Nie, Selvaraj Muthusamy, Zhibin Luo, Bin Liu

2023Organic Letters18 citationsDOI

Abstract

The deconstructive ring cleavage of cyclic thioethers is achieved through a Chan-Lam type process with boron compounds. The sequential hydroboration/ring cleavage process from alkynes offered a new route to the preparation of vinyl sulfides based on the developed conditions. Further exploration has demonstrated the versatility of nucleophiles, delivering various functionalized sulfides featuring linear frameworks.

Topics & Concepts

ChemistryHydroborationCleavage (geology)BoronNucleophileRing (chemistry)CopperCombinatorial chemistryPolymer chemistryOrganic chemistryStereochemistryCatalysisGeotechnical engineeringEngineeringFracture (geology)Sulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsCatalytic C–H Functionalization Methods
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