Direct C(sp3)-H functionalization of N-unprotected aliphatic amines represents one of the most efficient and straightforward strategies for amine synthesis.Despite some recent progress in this field,the NH2-directed y...Direct C(sp3)-H functionalization of N-unprotected aliphatic amines represents one of the most efficient and straightforward strategies for amine synthesis.Despite some recent progress in this field,the NH2-directed y-C(sp3)-H arylation of primary aliphatic amines exceptα-amino esters remained an unmet challenge.In this report,we established a simple and efficient method for site-selective C(sp3)-H arylation of primary aliphatic amines by aryl iodides.In 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 groups.The 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.展开更多
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。
文摘Direct C(sp3)-H functionalization of N-unprotected aliphatic amines represents one of the most efficient and straightforward strategies for amine synthesis.Despite some recent progress in this field,the NH2-directed y-C(sp3)-H arylation of primary aliphatic amines exceptα-amino esters remained an unmet challenge.In this report,we established a simple and efficient method for site-selective C(sp3)-H arylation of primary aliphatic amines by aryl iodides.In 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 groups.The 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.
