有氧催化氧化交叉偶联 - 取代苯胺和氨萘酚与酚类和萘酚。
Aerobic Catalyzed Oxidative Cross-Coupling of ,-Disubstituted Anilines and Aminonaphthalenes with Phenols and Naphthols.
机构信息
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.
出版信息
Org Lett. 2020 Mar 6;22(5):1765-1770. doi: 10.1021/acs.orglett.0c00046. Epub 2020 Feb 12.
Abstract
The cross-coupling of ,-dialkyl aniline and aminonaphthalenes with phenols and naphthols using a Cr-salen catalyst under aerobic conditions was developed. Notably, air serves as an effective oxidant affording products in high selectivity. Initial mechanistic studies suggest an outer-sphere oxidation of the aniline/aminonaphthalene partner, followed by nucleophilic attack of the phenol/naphthol. Single products were observed in most cases, whereas mixtures of C-C and C-O coupled products arose from reactions involving aminonapthalene and sterically unencumbered phenols.
摘要
在有氧条件下，使用 Cr-salen 催化剂实现了 -二烷基苯胺和氨基萘与苯酚和萘酚的交叉偶联。值得注意的是，空气作为有效氧化剂，以高选择性提供产物。初步的机理研究表明苯胺/氨基萘配体发生了外球氧化，随后酚/萘酚进行亲核进攻。在大多数情况下观察到单一产物，而涉及氨基萘和无空间位阻苯酚的反应则生成 C-C 和 C-O 偶联产物的混合物。
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