Peroxide-Free Pd(II)-Catalyzed Ortho Aroylation and Ortho Halogenation of Directing Arenes

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• 作者：Sourav Kumar Santra ; Arghya Banerjee ; Prakash Ranjan Mohanta ; Bhisma K. Patel
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：July 15, 2016
• 年：2016
• 卷：81
• 期：14
• 页码：6066-6074
• 全文大小：547K
• 年卷期：0
• ISSN：1520-6904

文摘

A Pd(II)-catalyzed peroxide-free ortho aroylation of directing arenes has been developed via cross dehydrogenative coupling (CDC) in the presence of the terminal oxidant Cu(OAc)₂·H₂O. Ortho aroylation of directing arenes proceeds via decarbonylation of the in situ generated phenyl glyoxal, which is obtained from 2-acetoxyacetophenone in the presence of the oxidant Cu(OAc)₂·H₂O. However, changing the oxidant to CuX₂ (X = Cl, Br) provided exclusive di-ortho-halogenated 2-arylbenzothiazoles. During the halogenation, CuX₂ served the dual role of a halogen source as well as a co-oxidant.