.png){kind=icon}
.png){kind=icon}
Return
Heptafluoroisopropyl iodide/silver(I)-mediated benzylic C(sp3)-H amination: direct access to N-alkylated benzimidazoles from simple hydrocarbons
.png){kind=icon}
PRE
AI
H
Y
W
J
朱
F
Z
Q
F
DOI：10.1016/j.tetlet.2025.155944.png)
.png){kind=icon}
Original request for help.png){kind=icon}
Share.png){kind=icon}
Save
Abstract
En 中文
An efficient one-pot heptafluoroisopropyl iodide/silver(I)-mediated cross-dehydrogenative N-H/benzylic C (sp3)-H coupling of benzimidazoles with simple benzylic hydrocarbons has been developed. This protocol enables the direct construction of C-N bonds from readily available substrates without prefunctionalization under mild conditions. Under the optimized conditions (Ag2O as the oxidant and i-C3F7I as a radical precursor, 100 degrees C, air), a broad range of N-alkylated benzimidazoles and related azoles are obtained in moderate to good yields with good tolerance to various functional groups. Mechanistic studies, including radical inhibition experiments and a kinetic isotope effect (k_H/k_D = 2.1), support a radical pathway in which benzylic and N-centered radicals are generated under fluorinated radical/silver(I) initiation and undergo radical-radical cross-coupling to form the C-N bond. This straightforward and operationally simple strategy provides a practical and complementary approach for the synthesis of benzimidazole derivatives via direct benzylic C(sp3)-H amination.
Keywords:
Heptafluoroisopropyl iodide initiation
Ag(D)-mediated cross-dehydrogenative coupling
CH activation of inert hydrocarbons Benzylic Cup)-H amination
Journal
T
IF:
1.5
Papers:
148
Citations:
4.2W
Organization
Cited Papers