Unexpected Phenol Production from Arylboronic Acids under Palladium-Free Conditions; Organocatalyzed Air Oxidation

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• 作者：Andrew N. Cammidge ; Victoria H. M. Goddard ; Christopher P. J. Schubert ; Hemant Gopee ; David L. Hughes ; Daniel Gonzalez-Lucas
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：November 18, 2011
• 年：2011
• 卷：13
• 期：22
• 页码：6034-6037
• 全文大小：743K
• 年卷期：v.13,no.22(November 18, 2011)
• ISSN：1523-7052

文摘

An intriguing class of quinones that efficiently catalyze the air oxidation (overall hydroxylation) of arylboronic acids to the corresponding phenol is reported. Autocatalysis in the parent system is particularly efficient and leads to rapid, quantitative synthesis of quinones such as 4 from boronic acid 1 at room temperature using air as stoichiometric oxidant. The efficiency results from a balance between two-stage conjugate addition and migration with each step driven by aromatization of a naphthalene fragment.