Selectfluor™-catalyzed oxidative cyclization of ynamides enables facile synthesis of oxazolidine-2,4-diones

Guangke He; Yuan Li; Zilun Yu; Zhaoqiang Chen; Yongming Tang; Guangliang Song; Teck Peng Loh

doi:10.1039/c9qo00845d

Selectfluor™-catalyzed oxidative cyclization of ynamides enables facile synthesis of oxazolidine-2,4-diones

Guangke He^*, Yuan Li, Zilun Yu, Zhaoqiang Chen, Yongming Tang, Guangliang Song, Teck Peng Loh

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

Abstract

A Selectfluor™-catalyzed oxidative cyclization of ynamides affording oxazolidine-2,4-diones in yields from 69%-94% is described. The reaction is run under air and exhibits excellent chemo-selectivity and functional group compatibility. Preliminary mechanistic studies reveal that the solvent DMSO acts as an oxidant, and the redox reaction of Selectfluor™ with DMSO generates the real active catalyst HBF₄in situ.

Original language	English
Pages (from-to)	3644-3648
Number of pages	5
Journal	Organic Chemistry Frontiers
Volume	6
Issue number	21
DOIs	https://doi.org/10.1039/c9qo00845d
Publication status	Published - Nov 7 2019
Externally published	Yes

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© 2019 the Partner Organisations.

ASJC Scopus Subject Areas

Organic Chemistry

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title = "Selectfluor{\texttrademark}-catalyzed oxidative cyclization of ynamides enables facile synthesis of oxazolidine-2,4-diones",

abstract = "A Selectfluor{\texttrademark}-catalyzed oxidative cyclization of ynamides affording oxazolidine-2,4-diones in yields from 69%-94% is described. The reaction is run under air and exhibits excellent chemo-selectivity and functional group compatibility. Preliminary mechanistic studies reveal that the solvent DMSO acts as an oxidant, and the redox reaction of Selectfluor{\texttrademark} with DMSO generates the real active catalyst HBF4in situ.",

author = "Guangke He and Yuan Li and Zilun Yu and Zhaoqiang Chen and Yongming Tang and Guangliang Song and Loh, {Teck Peng}",

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T1 - Selectfluor™-catalyzed oxidative cyclization of ynamides enables facile synthesis of oxazolidine-2,4-diones

AU - He, Guangke

AU - Li, Yuan

AU - Yu, Zilun

AU - Chen, Zhaoqiang

AU - Tang, Yongming

AU - Song, Guangliang

AU - Loh, Teck Peng

PY - 2019/11/7

Y1 - 2019/11/7

N2 - A Selectfluor™-catalyzed oxidative cyclization of ynamides affording oxazolidine-2,4-diones in yields from 69%-94% is described. The reaction is run under air and exhibits excellent chemo-selectivity and functional group compatibility. Preliminary mechanistic studies reveal that the solvent DMSO acts as an oxidant, and the redox reaction of Selectfluor™ with DMSO generates the real active catalyst HBF4in situ.

AB - A Selectfluor™-catalyzed oxidative cyclization of ynamides affording oxazolidine-2,4-diones in yields from 69%-94% is described. The reaction is run under air and exhibits excellent chemo-selectivity and functional group compatibility. Preliminary mechanistic studies reveal that the solvent DMSO acts as an oxidant, and the redox reaction of Selectfluor™ with DMSO generates the real active catalyst HBF4in situ.

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JF - Organic Chemistry Frontiers

IS - 21

ER -

Selectfluor™-catalyzed oxidative cyclization of ynamides enables facile synthesis of oxazolidine-2,4-diones

Abstract

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