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タイトル: | Ni-Catalyzed Carboxylation of C(sp²)–S Bonds with CO₂: Evidence for the Multifaceted Role of Zn |
著者: | Yanagi, Tomoyuki Somerville, J. Rosie Nogi, Keisuke Martin, Ruben Yorimitsu, Hideki https://orcid.org/0000-0002-0153-1888 (unconfirmed) |
著者名の別形: | 柳, 智征 野木, 馨介 依光, 英樹 |
キーワード: | carboxylation nickel C−S cleavage carbon dioxide zinc |
発行日: | 7-Feb-2020 |
出版者: | American Chemical Society (ACS) |
誌名: | ACS Catalysis |
巻: | 10 |
号: | 3 |
開始ページ: | 2117 |
終了ページ: | 2123 |
抄録: | Nickel-catalyzed reductive carboxylation reactions of aryl electrophiles typically require the use of metallic reducing agents. At present, the prevailing perception is that these serve as both a source of electrons and as a source of Lewis acids that may aid CO₂ insertion into the Ni–C bond. Herein, we provide evidence for the in situ formation of organometallic species from the metallic reductant, a step that has either been ruled out or has been unexplored in catalytic carboxylation reactions with metal powder reductants. Specifically, we demonstrate that Zn(0) acts as a reductant and that Zn(II) generates arylzinc species that might play a role in the C(sp²)–S carboxylation of arylsulfonium salts. Overall, the reductive Ni-catalyzed C(sp²)–S carboxylation reaction proceeds under mild conditions in a non-amide solvent, displays a wide substrate scope, and can be applied to the formal para C–H carboxylation of arenes. |
著作権等: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acscatal.9b05141. The full-text file will be made open to the public on 15 January 2021 in accordance with publisher's 'Terms and Conditions for Self-Archiving'. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。 This is not the published version. Please cite only the published version. |
URI: | http://hdl.handle.net/2433/255855 |
DOI(出版社版): | 10.1021/acscatal.9b05141 |
出現コレクション: | 学術雑誌掲載論文等 |
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