Regioselective, Transition Metal-Free C–O Coupling Reactions Involving Aryne Intermediates

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• 作者：Yuyang Dong ; Michael I. Lipschutz ; T. Don Tilley
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：April 1, 2016
• 年：2016
• 卷：18
• 期：7
• 页码：1530-1533
• 全文大小：361K
• ISSN：1523-7052

文摘

A new transition-metal-free synthetic method for C–O coupling between various aryl halides and alkoxides is described. This type of transformation is typically accomplished using palladium catalysts containing a specialized phosphine ligand. The reactions reported here can be performed under mild, ambient conditions using certain potassium alkoxides and a range of aryl halides, with iodide and bromide derivatives giving the best results. A likely mechanistic pathway involves the in situ generation of an aryne intermediate, and directing groups on the aryl ring inductively control regioselectivity.