Reactions of HDDA-Derived Benzynes with Sulfides: Mechanism, Modes, and Three-Component Reactions

Junhua Chen, Vignesh Palani, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

55 Scopus citations

Abstract

We report here reactions of alkyl sulfides with benzynes thermally generated by the hexadehydro-Diels-Alder (HDDA) cycloisomerization. The initially produced 1,3-betaine (o-sulfonium/aryl carbanion) undergoes intramolecular proton transfer to generate a more stable S-aryl sulfur ylide. This can react in various manners, including engaging weak acids (HA) in the reaction medium. This can produce transient ion pairs ArSR2+A- that proceed to the products ArSR + RA. When cyclic sulfides are used, A- opens the ring and is incorporated into the product, an outcome that constitutes a versatile, three-component coupling process.

Original languageEnglish (US)
Pages (from-to)4318-4321
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number13
DOIs
StatePublished - Apr 20 2016

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