Synthesis of Allenyl Sulfones via a TBHP/TBAI-Mediated Reaction of Propargyl Alcohols with Sulfonyl Hydrazides

Zheng Yang, Wen Juan Hao, Shu Liang Wang, Jin Peng Zhang, Bo Jiang, Guigen Li, Shu Jiang Tu

Research output: Contribution to journalArticle

54 Scopus citations

Abstract

A new TBHP/TBAI-mediated reaction of propargyl alcohols with sulfonyl hydrazides in the presence of HOAc has been established, in which a wide variety of allenyl sulfones were obtained in moderate to excellent yields. Mechanistic studies indicate that this transformation involves HOAc-promoted sulfonohydrazide intermediate formation, sequential C-O, C-N, and N-S bond cleavage, and C-S bond formation. Significantly, this sulfonohylation proceeds in a radical process and shows highly functional group compatibility and excellent regioselectivity, with a short reaction time and inexpensive reagents.

Original languageEnglish
Pages (from-to)9224-9230
Number of pages7
JournalJournal of Organic Chemistry
Volume80
Issue number18
DOIs
StatePublished - Sep 18 2015

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