Mn(OAc)3-Promoted Sulfonation-ipso-Cyclization Cascade via the SO3 - Radical: The Synthesis of Spirocyclic Sulfonates

A radical sulfonation-ipso-cyclization cascade promoted by Mn(OAc)(3).2H(2)O using functionalized alkynes or alkenes and potassium metabisulfite (K2S2O5) 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.

Automated summary

A radical sulfonation-ipso-cyclization cascade promoted by Mn(OAc)(3).2H(2)O using functionalized alkynes or alkenes and potassium metabisulfite (K2S2O5) was reported. 30 spirocyclic sulfonates were synthesized under mild conditions. A modular synthesis approach was demonstrated for the preparation of various azaspiro[4,5]-trienone-based sulfonamides and sulfonate esters.