trans-Selective and Switchable Arene Hydrogenation of Phenol Derivatives,ACS Catalysis

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trans-Selective and Switchable Arene Hydrogenation of Phenol Derivatives
ACS Catalysis ( IF 11.3 ) Pub Date : 2020-09-15 , DOI: 10.1021/acscatal.0c03423
Marco Wollenburg ₁ , Arne Heusler ₁ , Klaus Bergander ₁ , Frank Glorius ₁

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A trans-selective arene hydrogenation of abundant phenol derivatives catalyzed by a commercially available heterogeneous palladium catalyst is reported. The described method tolerates a variety of functional groups and provides access to a broad scope of trans-configurated cyclohexanols as potential building blocks for life sciences and beyond in a one-step procedure. The transformation is strategically important because arene hydrogenation preferentially delivers the opposite cis-isomers. The diastereoselectivity of the phenol hydrogenation can be switched to the cis-isomers by employing rhodium-based catalysts. Moreover, a protocol for the chemoselective hydrogenation of phenols to cyclohexanones was developed.

中文翻译：

苯酚衍生物的反式和可选择性芳烃加氢

甲反式报告由市售的非均相钯催化剂催化丰富酚衍生物的芳烃-选择性加氢。所描述的方法可耐受多种功能基团，并在一站式过程中提供了广泛范围的反式配置环己醇作为生命科学及其他领域潜在的构建基块。由于芳烃氢化优先提供相反的顺式异构体，因此该转化在战略上很重要。通过使用铑基催化剂，可以将苯酚氢化的非对映选择性转变为顺式异构体。此外，开发了将苯酚化学选择性氢化成环己酮的方案。

更新日期：2020-10-02

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