Synthesis of β,β-Dithioketones by Merging C–C and C–S Bond Cleavage in [1 + 1 + 1 + 1 + 1 + 1] Annulation
Dong‐Sheng Yang, Xiang‐Long Chen, Chun‐Yan Wu, Bo‐Cheng Tang, Yong-Cheng Xiao, Yan‐Dong Wu, An‐Xin Wu
Abstract
An unconventional [1 + 1 + 1 + 1 + 1 + 1] annulation process was developed for the construction of β,β-dithioketones by merging C–C and C–S bond cleavage. In this reaction, rongalite concurrently served as triple C1 units, dual sulfur(II) synthons, and a reductant for the first time. Mechanism investigation indicated that the reaction involved the self-mediated valence state change of rongalite. By performing this step-economical method, the challenging construction of C 5 -substituted 1,3-dithiane can be achieved under mild and simple conditions.
Topics & Concepts
AnnulationSynthonChemistryBond cleavageCleavage (geology)Triple bondSulfurCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryCatalysisDouble bondEngineeringGeotechnical engineeringFracture (geology)Sulfur-Based Synthesis TechniquesChemical Synthesis and ReactionsSynthesis of heterocyclic compounds