4.7 Article

Copper-catalyzed, N-directed remote C(sp3)-H azidation and thiocyanation

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ORGANIC CHEMISTRY FRONTIERS
卷 8, 期 2, 页码 249-253

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d0qo01012j

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  1. Natural Science Foundation of the Jiangsu Higher Education Institutions of China [18KJA350001]
  2. Priority Academic Program Development of the Jiangsu Higher Education Institutes (PAPD)

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An efficient and general method for catalytic installation of azido and thiocyanato groups via remote C(sp(3))-H activation is described. The copper-catalyzed reaction proceeds through a cascade of single-electron transfer, favorable 1,5-hydrogen atom transfer, and C-N/C-S cross-coupling, providing distal azido and thiocyanato alkylamines. This reaction is applicable to various types of C(sp(3))-H functionalization and demonstrates excellent site-selectivity and functional-group compatibility.
An efficient and general method for the catalytic installation of azido and thiocyanato groups via remote C(sp(3))-H activation is described. The copper-catalyzed reaction proceeds through a cascade of single-electron transfer, favorable 1,5-hydrogen atom transfer, and C-N/C-S cross-coupling, thus providing the distal azido and thiocyanato alkylamines. This reaction could be applicable to primary, secondary, tertiary, and benzylic C(sp(3))-H functionalization, as well as demonstrating excellent site-selectivity and functional-group compatibility.

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