Isodesmic C(sp2)-H Iodination of 2-Phenethylamines Directed by Native Primary Amino Groups - Details

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The　site-selective　C-H　functionalization　of　native　phenethylamines　remains　a　significant　synthetic　challenge　due　to　the　strong　coordination　ability　of　the　primary　amine　group.　Herein,　a　palladium-catalyzed　isodesmic　C(sp2)-H　iodination　of　2-phenethylamines　directed　by　native,　unprotected　primary　amino　groups　is　described.　The　reaction　proceeds　under　mild　conditions　using　aryl　iodides　as　iodine　donors　and　exhibits　broad　functional　group　tolerance.　The　method　enables　efficient　mono-　and　di-iodination　of　simple　phenethylamines,　as　well　as　late-stage　diversification　of　phenylalanine　derivatives.　This　protocol　offers　a　practical　and　broadly　applicable　strategy　for　direct　aryl　iodide　synthesis　from　native　amines.　©　2025　American　Chemical　Society.

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[ 1 ] [Wang X.]College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 2 ] [Wang X.]State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou, 350002, China
[ 3 ] [He C.]College of Chemistry, Fuzhou University, Fuzhou, 350108, China
[ 4 ] [He C.]State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou, 350002, China
[ 5 ] [Zhou C.]State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou, 350002, China
[ 6 ] [Li G.]Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Zhang Jiang Institute for Advanced Study, Shanghai Jiao Tong University, Shanghai, 200240, China
[ 7 ] [Li S.]State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou, 350002, China
[ 8 ] [Zhang J.]State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou, 350002, China

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Organic Letters

ISSN： 1523-7060

Year： 2025

4 . 9 0 0

JCR@2023

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ESI Highly Cited Papers on the List： 0 Unfold All

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30 Days PV： 2

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