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钌催化的芳醇的交叉选择性不对称氧化偶联反应

Ruthenium-Catalyzed Cross-Selective Asymmetric Oxidative Coupling of Arenols.

作者信息

Hayashi Hiroki, Ueno Takamasa, Kim Chungsik, Uchida Tatsuya

机构信息

Faculty of Arts and Science , Kyushu University , 744 Motooka, Nishi-ku , Fukuoka 819-0395 , Japan.

Department of Chemistry, Graduate School of Science , Kyushu University , 744 Motooka, Nishi-ku , Fukuoka 819-0395 , Japan.

出版信息

Org Lett. 2020 Feb 21;22(4):1469-1474. doi: 10.1021/acs.orglett.0c00048. Epub 2020 Jan 27.

DOI:10.1021/acs.orglett.0c00048
PMID:31984748
Abstract

(Aqua)ruthenium(salen) complex achieved good to high chemo- and enantioselective oxidative cross-coupling of arenols. The catalytic system can be used to selectively produce -symmetric bis(arenol)s from the combination of C3- and C7-substituted 2-naphthols or phenols even when there is no significant difference in oxidation potential between the cross-coupling partners. This unique cross-selectivity is dominated by steric rather than electronic effects of the arenols and can be controlled by chemoselective single-electron oxidation and oxidative carbon-carbon bond formation.

摘要

(水合)钌(萨伦)配合物实现了对芳醇良好至高的化学和对映选择性氧化交叉偶联反应。该催化体系可用于从C3-和C7-取代的2-萘酚或酚类的组合中选择性地生成对称双(芳醇),即使交叉偶联伙伴之间的氧化电位没有显著差异。这种独特的交叉选择性由芳醇的空间效应而非电子效应主导,并且可以通过化学选择性单电子氧化和氧化碳-碳键形成来控制。

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