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Molecules 2015, 20(7), 13336-13353; doi:10.3390/molecules200713336

Iminoiodane- and Brønsted Base-Mediated Cross Dehydrogenative Coupling of Cyclic Ethers with 1,3-Dicarbonyl Compounds

1
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
2
School of Chemistry, Monash University, Clayton, Victoria 3800, Australia
3
State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Macao, China
4
Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong, China
5
Department of Chemistry, University of Warwick, Coventry CV4 7AL, UK
*
Author to whom correspondence should be addressed.
Academic Editor: Kei Saito
Received: 1 June 2015 / Revised: 13 July 2015 / Accepted: 14 July 2015 / Published: 22 July 2015
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)
View Full-Text   |   Download PDF [1074 KB, uploaded 22 July 2015]   |  

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. View Full-Text
Keywords: C–C bond formation; cross dehydrogenation coupling; 1,3-dicarbonyl compounds; iminoiodanes; metal-free catalysis C–C bond formation; cross dehydrogenation coupling; 1,3-dicarbonyl compounds; iminoiodanes; metal-free catalysis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Tejo, C.; Sim, X.R.; Lee, B.R.; Ayers, B.J.; Leung, C.-H.; Ma, D.-L.; Chan, P.W.H. Iminoiodane- and Brønsted Base-Mediated Cross Dehydrogenative Coupling of Cyclic Ethers with 1,3-Dicarbonyl Compounds. Molecules 2015, 20, 13336-13353.

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