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
Affiliations
Ciputra Tejo
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
Xiao Rong Sim
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
Bo Ra Lee
School of Chemistry, Monash University, Clayton, Victoria 3800, Australia
Benjamin James Ayers
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
Chung-Hang Leung
State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Macao, China
Dik-Lung Ma
Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong, China
Philip Wai Hong Chan
School of Chemistry, Monash University, Clayton, Victoria 3800, Australia
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.
