Journal
CHEMICAL SCIENCE
Volume 8, Issue 1, Pages 169-173Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6sc03169b
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Funding
- Shenzhen Government [JCYJ20150626110741712, JCYJ20150331100341865, JCYJ20140627145302109]
- Guangdong Government [S20120011226]
- National Science Foundation of China [21332005, 21571098]
- MOST of China [2014AA020512]
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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.
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