Sulfonamide-Trapping Reactions of Thermally Generated Benzynes

Yuanxian Wang, Lianyou Zheng, Thomas R. Hoye

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

Reactions of tethered, tertiary sulfonamides with thermally generated benzynes are reported. Typically, the N-S bonds in the substrates cleave, and saturated heterocycles [tetrahydroquinolines (n = 2) and indolines (n = 1)] are formed. The process is accompanied by either sulfonyl transfer or desulfonylation from a zwitterionic intermediate, with the favored pathway being largely dependent upon the size (5- vs 6-membered) of the N-containing ring in the zwitterion.

Original languageEnglish (US)
Pages (from-to)7145-7148
Number of pages4
JournalOrganic Letters
Volume20
Issue number22
DOIs
StatePublished - Nov 16 2018

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