Disubstituted Pyridines: The Double-Coupling Approach

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• 作者：Scott T. Handy ; Thomas Wilson ; Aaron Muth
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：October 26, 2007
• 年：2007
• 卷：72
• 期：22
• 页码：8496 - 8500
• 全文大小：74K
• 年卷期：v.72,no.22(October 26, 2007)
• ISSN：1520-6904

文摘

A one-pot procedure leading to disubstituted pyridines from the starting dibromopyridines is described.Key features include the ability to couple a range of aryl and even alkenylboronic acids at the 2,3 and/or2,5 positions with excellent regiocontrol under a standard set of conditions. Further, isolated yields aregreatly improved by the use of neutral alumina in place of silica for product purification. Finally, theintrinsic electronic bias of the pyridine ring can be overcome by using a bromoiodopyridine.