A facile access for the C-N bond formation by transition metal-free oxidative coupling of benzylic C-H bonds and amides文档.pdf

SCIENCE CHINA Chemistry • ARTICLES • August 2015 Vol.58 No.8: 1323–1328 · SPECIAL ISSUE · CH bond activation doi: 10.1007/s11426-015-5381-2 A facile access for the C–N bond formation by transition metal-free oxidative coupling of benzylic C–H bonds and amides 1 1 1 1* 1,2* Jie Liu , Heng Zhang , Hong Yi , Chao Liu Aiwen Lei 1College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China 2National Research Centre for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, China Received January 14, 2015; accepted January 27, 2015; published online March 24, 2015 Using 2,3-dichloro-5,6-dicyano-p -benzoquinone (DDQ) as the oxidant, we communicate an efficient oxidative C–N coupling of benzylic C–H bonds with amides to afford a series of amination products in good yields. A wide range of functional groups as well as various sulfonamides and carboxamides are well tolerated. Moreover, this reaction involves both the challenging C–H functionalization and C–N bond formation. oxidative coupling, C–N bond formation, amination, C–H functionalization 1 Introduction C–H amination reactions. Due to the presence of transition- metal impurities in the final products and/or the costly