Site-Selective Aliphatic C鈥揌 Bromination Using N-Bromoamides and Visible Light

详细信息    查看全文

• 作者：Valerie A. Schmidt ; Ryan K. Quinn ; Andrew T. Brusoe ; Erik J. Alexanian
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：October 15, 2014
• 年：2014
• 卷：136
• 期：41
• 页码：14389-14392
• 全文大小：344K
• ISSN：1520-5126

文摘

Transformations that selectively functionalize aliphatic C鈥揌 bonds hold significant promise to streamline complex molecule synthesis. Despite the potential for site-selective C鈥揌 functionalization, few intermolecular processes of preparative value exist. Herein, we report an approach to unactivated, aliphatic C鈥揌 bromination using readily available N-bromoamide reagents and visible light. These halogenations proceed in useful chemical yields, with substrate as the limiting reagent. The site selectivities of these radical-mediated C鈥揌 functionalizations are comparable (or superior) to the most selective intermolecular C鈥揌 functionalizations known. With the broad utility of alkyl bromides as synthetic intermediates, this convenient approach will find general use in chemical synthesis.