Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 13, Pages 6143-6152Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo500859b
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Funding
- NSFC [21372002, 21232007]
- Open Foundation of Jiangsu Key Laboratory [K201314]
- PAPD of Jiangsu Province
- Qing Lan Project
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The first organocatalytic oxyarylation of styrenes has been established through a cascade of vinylogous Michael adclition/alkoxyl transfer reactions of o- or p-hydroxylstyrenes with quinone imine ketals. The process leads to a highly chemo- and regioselective oxyarylation of styrenes and provides access to m-alkylated anilines in generally high yields and excellent diastereoselectivity (up to 99% yield, >95:5 dr). An investigation of the reaction pathway revealed that the existence and position of the hydroxyl group of styrene played crucial roles in the cascade reaction, suggesting that the two reactants were simultaneously activated by binaphthyl-derived phosphoric acid via hydrogen bonding interactions and long-distance conjugative effects. In addition, the activating group of the hydroxyl functionality in the products can be easily removed or transformed, demonstrating the applicability and utility of this strategy in styrene oxyarylation and in the synthesis of styrene-based compounds.
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