O 2 -Controlled Acid-Mediated Sulfenylation/Cyclization of Tethered Malononitriles and Sulfides toward Divergent Synthesis of Mono/Dithio-cyclopentenones

Organic Letters 2026

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Authors: Dandan He, Sha Wu, Xiong Wen, Fei Jiang, Huili Li, Ting Xiao, Linjing Wu, Tao Ling, Xiangchun Shen
DOI: 10.1021/acs.orglett.5c04770
Cited by: 0
References: 25

Abstract

We have described an efficient, O 2 -controlled acid-mediated reaction that enables divergent synthesis of mono- and dithio-cyclopentenones from tethered malononitriles and sulfides. Monosulfenylated products are obtained directly with HCl in good to excellent yields, whereas the additional use of O 2 as the oxidant and a one-pot two-step operation favors the formation of disulfenylated analogs. This method features a broad substrate scope, excellent regioselectivities, mild conditions, and green oxidant. Gram-scale synthesis and product diversification demonstrate the practical utility of this protocol.

Fields of Study & Subjects

Sulfur-Based Synthesis Techniques Synthesis and Reactivity of Sulfur-Containing Compounds Organic Chemistry Synthesis Methods

Publication details

Journal / source
Organic Letters
Volume
28
Issue
4
Pages
1164–1169
Publication date
15 January 2026
Language
EN