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; 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

Molecules. 2015 Jul 22;20(7):13336-53. doi: 10.3390/molecules200713336.

Authors

Ciputra Tejo¹, Xiao Rong Sim², Bo Ra Lee³, Benjamin James Ayers⁴, Chung-Hang Leung⁵, Dik-Lung Ma⁶, Philip Wai Hong Chan^{7

8}

Affiliations

¹ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore. cipu0002@e.ntu.edu.sg.
² Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore. xrsim1@e.ntu.edu.sg.
³ School of Chemistry, Monash University, Clayton, Victoria 3800, Australia. bora.lee@monash.edu.
⁴ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore. benayers@ntu.edu.sg.
⁵ State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Macao, China. duncanleung@umac.mo.
⁶ Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong, China. edmondma@hkbu.edu.hk.
⁷ School of Chemistry, Monash University, Clayton, Victoria 3800, Australia. phil.chan@monash.edu.
⁸ Department of Chemistry, University of Warwick, Coventry CV4 7AL, UK. phil.chan@monash.edu.

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.

Keywords: 1,3-dicarbonyl compounds; C–C bond formation; cross dehydrogenation coupling; iminoiodanes; metal-free catalysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Ethers, Cyclic / chemical synthesis*
Ethers, Cyclic / chemistry*

Substances

Ethers, Cyclic