Silver-catalysed direct amination of unactivated C–H bonds of functionalized molecules

• Published in: Nature communications 2014-08, Vol.5 (1), p.4707-4707, Article 4707
• Main Authors: Yang, Mingyu, Su, Bo, Wang, Yang, Chen, Kang, Jiang, Xingyu, Zhang, Yun-Fei, Zhang, Xi-Sha, Chen, Guihua, Cheng, Ye, Cao, Zhichao, Guo, Qing-Yun, Wang, Lushun, Shi, Zhang-Jie
• Format: Article
• Language: English
• Subjects: 140/131; 639/638/403; 639/638/439; 639/638/77; Humanities and Social Sciences; multidisciplinary; Science; Science (multidisciplinary)
• ISSN: 2041-1723; 2041-1723
• DOI: 10.1038/ncomms5707

Carbon–nitrogen bond formation from inert C–H bonds is an ideal organic transformation and a highly desirable method for the synthesis of N-containing molecules due to its high efficiency and atom economy. In this report, we develop a general reaction to achieve an unprecedented selective intramolecular amination of unactivated C–H bond in the absence of complex directing groups. Functionalized heterocyclic products are built up from readily available linear amines through simple and reliable silver catalysis, representing a new silver-based C–H functionalization. This method displays preference for primary sp 3 C–H bonds and exhibits distinct chemo- and regioselectivity compared to existing methods of direct amination (Hofmann–Löffler–Freytag reaction and nitrene insertion). The study highlights the manipulation of unfunctionalized groups in organic molecules to furnish complex structural units in the natural and bioactive molecules. Functionalizing unactivated carbon–hydrogen bonds is a powerful and atom efficient method to introduce functionality into a molecule. Here, the authors show activation and intramolecular amination of primary C–H bonds using a silver catalyst.