Selective functionalisation of aromatic alcohols with supramolecularly regulated gold(I) catalysts,Organic Chemistry Frontiers

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Selective functionalisation of aromatic alcohols with supramolecularly regulated gold(I) catalysts
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-05-20 , DOI: 10.1039/d0qo00416b
Lucas Carreras _{1,

2,

3} , Antonio Franconetti _{3,

4,

5,

6} , Arnald Grabulosa _{3,

7,

8,

9,

10} , Antonio Frontera _{3,

4,

5,

6} , Anton Vidal-Ferran _{1,

2,

3,

7,

8}

Affiliation

Phosphite-based Au(I) catalytic systems containing an array of structurally diverse polyether-based regulation sites were designed and synthesised. These catalysts have been successfully tested in the Au(I)-catalysed C–H functionalisation of phenols and related derivatives with gold–carbenes derived from diazo compounds. Regulation of the steric congestion around the catalytic Au(I) centre via ion–dipole interactions with an external regulation agent led to an enhancement of both the activity and selectivity of the reaction. This new approach in supramolecular gold(I) catalysis has been applied to the derivatisation of an array of substituted phenols and related substrates and to the preparation of an advanced synthetic intermediate of the anticancer agent tamoxifen. The effects of the regulation agent on the selectivity and yield of the reaction have been studied and rationalised using DFT-D calculations.

中文翻译：

超分子调节的金（I）催化剂对芳香族醇的选择性官能化

设计并合成了基于亚磷酸盐的Au（I）催化体系，该体系包含一系列结构多样的基于聚醚的调控位点。这些催化剂已经在Au（I）催化的苯酚和相关衍生物与重氮化合物衍生的金卡宾的CH官能化中进行了成功的测试。通过与外部调节剂的离子-偶极相互作用，催化Au（I）中心周围的空间拥塞的调节导致反应的活性和选择性都得到增强。在超分子黄金（这种新方法我）催化已应用于一系列取代酚和相关底物的衍生化以及抗癌药他莫昔芬的先进合成中间体的制备。使用DFT-D计算研究了调节剂对反应选择性和反应收率的影响并使其合理化。

更新日期：2020-06-30

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