Single-Electron-Transfer Strategy for Reductive Radical Cyclization: Fe(CO)5and Phenanthroline System.
An electron-transfer strategy using low-valent iron pentacarbonyl [Fe(CO)5] to generate radical species from alkyl iodides was achieved. A range of pyrrolidines, tetrahydrofurans, and carbocycles were synthesized via 5-exo cyclization reactions of alkyl radical intermediates generated by electron transfer from a system involving Fe(CO)5, 1,10-phenanthroline, and diisopropylamine. Moreover, tandem addition reactions with Michael acceptors were also explored. Photophysical and electrochemical studies support a mechanism that involves electron transfer from the low-valent Fe reductant to alkyl iodide.
Department of Applied Chemistry, Kyung Hee University , Yongin 17104, Korea.
Joon Young
JY
Hwang
Department of Applied Chemistry, Kyung Hee University , Yongin 17104, Korea.
Jong Hwa
JH
Baek
Department of Applied Chemistry, Kyung Hee University , Yongin 17104, Korea.
Tae Il
TI
Shin
Department of Applied Chemistry, Kyung Hee University , Yongin 17104, Korea.
Jung Ha
JH
Shin
Department of Applied Chemistry, Kyung Hee University , Yongin 17104, Korea.
Jae Won
JW
Oh
Department of Applied Chemistry, Kyung Hee University , Yongin 17104, Korea.
Kwang Pyo
KP
Kim
Division of Chemical Engineering and Materials Science, Ewha Womans University , Seoul 03760, Korea.
Youngmin
Y
You
Department of Applied Chemistry, Kyung Hee University , Yongin 17104, Korea.
Eun Joo
EJ
Kang