Iminoiodane- and Brønsted base-mediated cross dehydrogenative coupling of cyclic ethers with 1,3-dicarbonyl compounds

Ciputra Tejo; Xiao Rong Sim; Bo Ra Lee; Benjamin James Ayers; Chung Hang Leung; Edmond Dik Lung MA; Philip Wai Hong Chan

doi:10.3390/molecules200713336

Iminoiodane- and Brønsted base-mediated cross dehydrogenative coupling of cyclic ethers with 1,3-dicarbonyl compounds

Ciputra Tejo, Xiao Rong Sim, Bo Ra Lee, Benjamin James Ayers, Chung Hang Leung, Edmond Dik Lung MA, Philip Wai Hong Chan^*

^*Corresponding author for this work

Department of Chemistry

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

7 Citations (Scopus)

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Abstract

A one-pot, two-step approach to prepare 2-tetrahydrofuran and -pyran substituted 1,3-dicarbonyl compounds by PhI=NTs-mediated amination/Brønsted base-catalyzed cross dehydrogenative coupling (CDC) reaction of the cyclic ether and 1,3-dicarbonyl derivative under mild conditions is reported. The reaction is compatible with a variety of cyclic ethers and 1,3-dicarbonyl compounds, affording the corresponding coupled products in moderate to good yields of up to 80% over two steps.

Original language	English
Pages (from-to)	13336-13353
Number of pages	18
Journal	Molecules
Volume	20
Issue number	7
DOIs	https://doi.org/10.3390/molecules200713336
Publication status	Published - 1 Jul 2015

Scopus Subject Areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

User-Defined Keywords

1,3-dicarbonyl compounds
C-C bond formation
Cross dehydrogenation coupling
Iminoiodanes
Metal-free catalysis

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title = "Iminoiodane- and Br{\o}nsted base-mediated cross dehydrogenative coupling of cyclic ethers with 1,3-dicarbonyl compounds",

abstract = "A one-pot, two-step approach to prepare 2-tetrahydrofuran and -pyran substituted 1,3-dicarbonyl compounds by PhI=NTs-mediated amination/Br{\o}nsted base-catalyzed cross dehydrogenative coupling (CDC) reaction of the cyclic ether and 1,3-dicarbonyl derivative under mild conditions is reported. The reaction is compatible with a variety of cyclic ethers and 1,3-dicarbonyl compounds, affording the corresponding coupled products in moderate to good yields of up to 80% over two steps.",

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AU - Tejo, Ciputra

AU - Sim, Xiao Rong

AU - Lee, Bo Ra

AU - Ayers, Benjamin James

AU - Leung, Chung Hang

AU - MA, Edmond Dik Lung

AU - Chan, Philip Wai Hong

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N2 - A one-pot, two-step approach to prepare 2-tetrahydrofuran and -pyran substituted 1,3-dicarbonyl compounds by PhI=NTs-mediated amination/Brønsted base-catalyzed cross dehydrogenative coupling (CDC) reaction of the cyclic ether and 1,3-dicarbonyl derivative under mild conditions is reported. The reaction is compatible with a variety of cyclic ethers and 1,3-dicarbonyl compounds, affording the corresponding coupled products in moderate to good yields of up to 80% over two steps.

AB - A one-pot, two-step approach to prepare 2-tetrahydrofuran and -pyran substituted 1,3-dicarbonyl compounds by PhI=NTs-mediated amination/Brønsted base-catalyzed cross dehydrogenative coupling (CDC) reaction of the cyclic ether and 1,3-dicarbonyl derivative under mild conditions is reported. The reaction is compatible with a variety of cyclic ethers and 1,3-dicarbonyl compounds, affording the corresponding coupled products in moderate to good yields of up to 80% over two steps.

KW - 1,3-dicarbonyl compounds

KW - C-C bond formation

KW - Cross dehydrogenation coupling

KW - Iminoiodanes

KW - Metal-free catalysis

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Iminoiodane- and Brønsted base-mediated cross dehydrogenative coupling of cyclic ethers with 1,3-dicarbonyl compounds

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