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

6 Citations (Scopus)

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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10.3390/molecules200713336

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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.",

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

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Iminoiodane- and Brønsted base-mediated cross dehydrogenative coupling of cyclic ethers with 1,3-dicarbonyl compounds. / Tejo, Ciputra; Sim, Xiao Rong; Lee, Bo Ra; Ayers, Benjamin James; Leung, Chung Hang; MA, Edmond Dik Lung; Chan, Philip Wai Hong.

In: Molecules, Vol. 20, No. 7, 01.07.2015, p. 13336-13353.

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

TY - JOUR

T1 - Iminoiodane- and Brønsted base-mediated cross dehydrogenative coupling of cyclic ethers with 1,3-dicarbonyl compounds

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

PY - 2015/7/1

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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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JF - Molecules

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IS - 7

ER -

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

Abstract

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