Native amine-directed site-selective C(sp^3)-H arylation of primary aliphatic amines with aryl iodides

作     者：Pranab KPramanick Zhibing Zhou Zhenlin Hou Yufei Ao Bo Yao Pranab K.Pramanick;Zhibing Zhou;Zhenlin Hou;Yufei Ao;Bo Yao

作者机构：MOE Key Laboratory of Cluster ScienceBeijing Key Laboratory of Photoelectronic-Electrophotonic Conversion MaterialsSchool of Chemistry and Chemical EngineeringBeijing Institute of TechnologyBeijing 102488China Beijing National Laboratory for Molecular SciencesCAS Key Laboratory of Molecular Recognition and FunctionInstitute of ChemistryChinese Academy of SciencesBeijing 100190China 

出 版 物：《Chinese Chemical Letters》 (中国化学快报（英文版）)

年 卷 期：2020年第31卷第5期

页      面：1327-1331页

核心收录：

学科分类：081702[工学-化学工艺] 08[工学] 0817[工学-化学工程与技术] 0703[理学-化学] 

基　　金：the National Natural Science Foundation of China(No.21502006) Beijing National Laboratory for Molecular Sciences and Beijing Institute of Technology(BIT)for financial support 

主　　题：Primary aliphatic amine Amino ether C(sp3)-H arylation Palladium catalysis Free amino group 

摘      要：Direct C(sp3)-H functionalization of N-unprotected aliphatic amines represents one of the most efficient and straightforward strategies for amine *** some recent progress in this field,the NH2-directed y-C(sp3)-H arylation of primary aliphatic amines exceptα-amino esters remained an unmet *** this report,we established a simple and efficient method for site-selective C(sp3)-H arylation of primary aliphatic amines by aryl *** the presence of only 5 mol%Pd(OAc)2,a wide range of aliphatic amines including O-benzyl and O-silyl amino alcohols were arylated at y-orδ-positions by aryl iodides containing a broad scope of functional *** synthetic application of this method had also been demonstrated by large-scale synthesis,the synthesis of a fingolimod analogue,and the conjugation with natural D-menthol and fluorescent 1,8-naphthalimide.