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Paper | Special issue | Vol 97, No. 1, 2018, pp.218-231
Published online, 18th May, 2018
DOI: 10.3987/COM-17-S(T)4
Palladium-Catalyzed Selective Formation of Substituted Pyrroles from Alkene-tethered Cyclic Oxime Esters

Kazuhiro Okamoto,* Tomohiro Oda, Gaku Matsushita, Takuya Shimbayashi, Kohei Sasakura, and Kouichi Ohe*

*Deparment of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai-katsura, Nishikyo, Kyoto 615-8510, Japan

Abstract

Isoxazol-5(4H)-ones were used as nitrene precursors for the selective formation of trisubstituted pyrroles by applying a palladium-catalyzed decarboxylative ring-reconstruction method. The use of bulky biaryl-type monophosphine ligands was effective for improving the selectivity. Deuterium-labeling experiments suggested a mechanism involving -hydride elimination followed by reductive elimination from an aza--allyl intermediate.