Angel Rentería-Gómez, Rubén O Torres-Ochoa, Pierre Palamini, Raphael Simonet-Davin, Qian Wang, J. Waser, Jieping Zhu
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引用次数: 0
Abstract
The generation of benzylic radicals through hydrogen atom abstraction (HAT) has been a recent research focus and various C(sp3)‐H bond functionalization protocols have been developed relying on this elementary step. We report herein copper‐ and iron‐catalyzed C(sp3)‐H benzylic azidation reactions using mCPBA and NFSI as oxidant, respectively, and TMSN3 as azide source. The reaction is thought to be initiated via intermolecular abstraction of benzylic hydrogen by the in situ generated heteroatom‐centered radicals. The Fe(OTf)3‐catalyzed azidation protocol displays good chemoselectivity as it takes place preferentially at the secondary and tertiary benzylic C(sp3)‐H bonds over the primary benzylic and tertiary aliphatic carbons. Efforts on the development of catalytic enantioselective processes are also documented.
期刊介绍：
Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance.
Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.
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