Synthesis of Pinacol Arylboronates from Aromatic Amines: A Metal-Free Transformation

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• 作者：Di Qiu ; Liang Jin ; Zhitong Zheng ; He Meng ; Fanyang Mo ; Xi Wang ; Yan Zhang ; Jianbo Wang
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：March 1, 2013
• 年：2013
• 卷：78
• 期：5
• 页码：1923-1933
• 全文大小：513K
• 年卷期：v.78,no.5(March 1, 2013)
• ISSN：1520-6904

文摘

A metal-free borylation process based on Sandmeyer-type transformation using arylamines derivatives as the substrates has been developed. Through optimization of the reaction conditions, this novel conversion can be successfully applied to a wide range of aromatic amines, affording borylation products in moderate to good yields. Various functionalized arylboronates, which are difficult to access by other methods, can be easily obtained with this metal-free transformation. Moreover, this transformation can be followed by Suzuki鈥揗iyaura cross-coupling without purification of the borylation products, which enhances the practical usefulness of this method. A possible reaction mechanism involving radical species has been proposed.