Unified synthesis of mono/bis-arylated phenols via RhIII-catalyzed dehydrogenative coupling.
نویسندگان
چکیده
2,6-Bis-arylated phenols are rarely reported and are synthetically challenging. Directed C-H functionalization reactions, using a directing group (DG), might provide a convenient solution to their synthesis. However, this strategy usually results in partial cleavage of the directing group, preventing further/second C-H activation cascades. Herein we report a general strategy that allows for the precise control of the oxidation pathways so that directing groups can be either preserved or cleaved. We found that N-phenoxyacetamides could undergo ortho-arylation reactions with or without an external oxidant, yielding products with different oxidation states, notably the rare bis-arylated phenols. Notably, a unique rhodacycle intermediate was isolated, characterized by X-ray crystallography, and confirmed to be an active catalyst. Switching between internal and external oxidation could be a general strategy in diverse directed C-H functionalization reactions to realize bis-functionalized products.
منابع مشابه
Unified synthesis of mono/bis-arylated phenols via RhIII-catalyzed dehydrogenative coupling† †Electronic supplementary information (ESI) available: Experimental procedures and characterization data for all new compounds. CCDC 1047606, 1426755, 1438599 and 1442845. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6sc03169b Click here for additional data file. Click here for additional data file.
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ورودعنوان ژورنال:
- Chemical science
دوره 8 1 شماره
صفحات -
تاریخ انتشار 2017