Palladium(II)-Catalyzed Annulation between ortho-Alkenylphenols and Allenes. Key Role of the Metal Geometry in Determining the Reaction Outcome

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• 作者：Noelia Casanova ; Karina P. Del Rio ; Rebeca García-Fandiño ; José L. Mascareñas ; Moisés Gulías
• 刊名：ACS Catalysis
• 出版年：2016
• 出版时间：May 6, 2016
• 年：2016
• 卷：6
• 期：5
• 页码：3349-3353
• 全文大小：446K
• 年卷期：0
• ISSN：2155-5435

文摘

2-Alkenylphenols react with allenes, upon treatment with catalytic amounts of Pd(II) and Cu(II), to give benzoxepine products in high yields and with very good regio- and diastereoselectivities. This contrasts with the results obtained with Rh catalysts, which provided chromene-like products through a pathway involving a β-hydrogen elimination step. Computational studies suggest that the square planar geometry of the palladium is critical to favor the reductive elimination process required for the formation of the oxepine products.