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Chemoselective Synthesis of Sulfenylated Spiroindolenines from Indolyl-ynones via Organosulfenyl Chloride-Mediated Dearomatizing Spirocyclization

Beibei Zhang, Xiaoxian Li, Zhenkang Ai, Bingyue Zhao, Zhenyang Yu, Yunfei Du

2021Organic Letters17 citationsDOI

Abstract

A metal-free sulfenylation/spirocyclization of indolyl-ynones realized by organosulfenyl chloride, generated in situ from the reaction of disulfides and PhICl2, is presented. This cascade one-pot process enables a chemoselective synthesis of diverse sulfenylated spiroindolenines depending on the substituent pattern at the two-position of indolyl-ynones.

Topics & Concepts

ChemistrySubstituentChlorideCombinatorial chemistryOrganic chemistrySulfur-Based Synthesis TechniquesSynthesis of Indole DerivativesChemical Synthesis and Reactions
Chemoselective Synthesis of Sulfenylated Spiroindolenines from Indolyl-ynones via Organosulfenyl Chloride-Mediated Dearomatizing Spirocyclization | Litcius