Mechanistic Studies into Visible Light-Driven Carboxylation of Aryl Halides/Triflates by the Combined Use of Palladium and Photoredox Catalysts

• Naoyuki Toriumi

  Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8551 , Japan

• Katsuya Shimomaki

  Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8551 , Japan

• Joaquim Caner

  Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8551 , Japan

• Kei Murata

  Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8551 , Japan

• Ruben Martin

  Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona , Spain

• Nobuharu Iwasawa

  Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8551 , Japan

抄録

The reaction mechanism of palladium-catalyzed visible light-driven carboxylation of aryl halides and triflates with a photoredox catalyst was examined in detail. Experimental and theoretical studies indicated that the active species for photoredox-catalyzed reduction was cationic ArPd(II)+ species to generate nucleophilic ArPd(I) or its further reduced ArPd(0)− species, which reacted with CO2 to give carboxylic acids. Hydrodehalogenated compounds, main byproducts in this carboxylation, were thought to be generated by protonation of these reduced species.

収録刊行物

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 94 (7), 1846-1853, 2021-06-05

  Oxford University Press (OUP)

キーワード

• General Chemistry

詳細情報

• CRID: 1360289145423247232
• NII論文ID: 130008076891
• DOI: 10.1246/bcsj.20210151
• ISSN: 13480634
• ISSN: 00092673
• Web Site: https://academic.oup.com/bcsj/article-pdf/94/7/1846/56311139/bcsj.20210151.pdf
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