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Citation: Pramanick Pranab K., Zhou Zhibing, Hou Zhenlin, Ao Yufei, BoYao. Native amine-directed site-selective C(sp3)-H arylation of primary aliphatic amines with aryl iodides[J]. Chinese Chemical Letters, ;2020, 31(5): 1327-1331. doi: 10.1016/j.cclet.2019.10.034 shu

Native amine-directed site-selective C(sp3)-H arylation of primary aliphatic amines with aryl iodides

  • a.

    MOE Key Laboratory of Cluster Science, Beijing Key Laboratory of Photoelectronic-Electrophotonic Conversion Materials, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 102488, China

  • b.

    Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China

    *Corresponding author at: MOE Key Laboratory of Cluster Science, Beijing Key Laboratory of Photoelectronic-Electrophotonic Conversion Materials, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 102488, China.
    E-mail address: yaobo@bit.edu.cn (B. Yao).
    1The authors contributed equally to the work.
  • Received Date: 11 September 2019
    Revised Date: 23 October 2019
    Accepted Date: 28 October 2019
    Available Online: 2 November 2019

Figures(4)

  • 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 γ-C(sp3)-H arylation of primary aliphatic amines except α-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 γ-or δ-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.
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