N, N-Diethyl O-Carbamate: Directed Metalation Group and Orthogonal Suzuki− Miyaura Cross-Coupling Partner

A Antoft-Finch, T Blackburn…

文献索引：Antoft-Finch, Aurora; Blackburn, Tom; Snieckus, Victor Journal of the American Chemical Society, 2009 , vol. 131, # 49 p. 17750 - 17752

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被引用次数: 162

摘要

The first Suzuki− Miyaura cross-coupling of an aryl O-carbamate, a versatile and powerful directed metalation group (DMG) in directed ortho metalation (D o M) chemistry, is described using the inexpensive, bench-stable catalyst NiCl2 (PCy3) 2. Broad synthetic scope and good efficiency are demonstrated for aryl and heteroaryl O-carbamates. The role of water and hydrolysis equilibrium between free boronic acid and boroxine was established to be ...