Mn(OAc)<sub>3</sub>-Promoted Sulfonation–<i>ipso</i>-Cyclization Cascade via the SO<sub>3</sub><sup>–</sup> Radical: The Synthesis of Spirocyclic Sulfonates
Yan Zhang, Bingxu Han, Xin Gu, Kaixuan Wang, Shuai Liang
Abstract
A radical sulfonation– ipso -cyclization cascade promoted by Mn(OAc) 3 ·2H 2 O using functionalized alkynes or alkenes and potassium metabisulfite (K 2 S 2 O 5 ) is reported. A total of 30 spirocyclic sulfonates were synthesized under mild conditions. We also demonstrate a modular synthesis approach in multiple steps for the preparation of various azaspiro[4,5]-trienone-based sulfonamides and sulfonate esters.
Topics & Concepts
CascadeChemistryRadical cyclizationMedicinal chemistryChromatographySulfur-Based Synthesis TechniquesOrganic and Inorganic Chemical ReactionsChemical Synthesis and Reactions