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Palladium‐Catalyzed Arylation of (Di)azinyl Aldoxime Ethers by Aryl Iodides: Stereoselective Synthesis of Unsymmetrical ( E )‐(Di)azinylaryl Ketoxime Ethers
Author(s) -
Gou Quan,
Deng Bin,
Qin Jun
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501758
Subject(s) - chemistry , palladium , aryl , catalysis , stereoselectivity , medicinal chemistry , organic chemistry , combinatorial chemistry , stereochemistry , alkyl
The first example of direct arylation of (di)azinyl aldoxime ethers by aryl iodides is reported. The reaction produces, in a single step, a variety of geometrically pure unsymmetrical ( E )‐(di)azinylaryl ketoxime ethers, a class of nitrogenated motifs that have found wide applications in medicinal and organic chemistry but are difficult to access using conventional procedure. The utility of the method is further illustrated in a formal synthesis of the Merck melanin‐concentrating hormone 1 receptor antagonist.