Organic Chemistry Laboratory, Nagoya University

“Palladium-Catalyzed Decarbonylative Cross-Coupling of Azinecarboxylates with Arylboronic Acids”

Muto, K.; Hatakeyama, T.; Itami, K*; Yamaguchi, J.* Org. Lett. 2016, DOI: 10.1021/acs.orglett.6b02556

The first palladium-catalyzed decarbonylative coupling of phenyl 2-azinecarboxylates and arylboronic acids is presented. The key for the development of this decarbonylative coupling is the use of Pd/dcype as a catalyst. A wide range of 2-azinecarboxylates can undergo the present coupling reaction to afford 2-arylazines. By combination with previously reported nickel-catalyzed decarbonylative coupling, we achieved a chemo-selective sequential decarbonylative coupling of pyridine dicarboxylate to synthesize 2,4-diaryl pyridine.