α-Arylation of Ketimines with Aryl Sulfides at a Low Palladium Catalyst Loading
Dr. Ke Gao
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Hideki Yorimitsu
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan
Search for more papers by this authorProf. Dr. Atsuhiro Osuka
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan
Search for more papers by this authorDr. Ke Gao
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Hideki Yorimitsu
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan
Search for more papers by this authorProf. Dr. Atsuhiro Osuka
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto, 606-8502 Japan
Search for more papers by this authorGraphical Abstract
Aryl sulfides, although typically poisonous to transition-metal catalysts, serve as aryl electrophiles in the catalytic α-arylation of ketimines. Low catalyst loadings (down to 0.5 mol %) of a Pd–NHC complex are sufficient for efficient arylation. α-Arylated ketimine products were used to synthesize various azaarenes including 2,3-diarylpyrroles.
Abstract
Instead of using aryl halides, aryl sulfides, typically poisonous to transition-metal catalysts, were found to serve as aryl electrophiles in the catalytic α-arylation of ketimines, a class of carbonyl derivatives. Low catalyst loadings (down to 0.5 mol %) of a palladium–NHC complex are sufficient for efficient arylation. α-Arylated ketimine products are useful for the synthesis of various azaarenes, including 2,3-diarylpyrroles, an indole, and pyrrolediones.
Supporting Information
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