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Single-Electron-Transfer Strategy for Reductive Radical Cyclization: Fe(CO) 5 and Phenanthroline System.

Single-Electron-Transfer Strategy for Reductive Radical Cyclization: Fe(CO) 5 and Phenanthroline System.

Authors :
Hwang JY
Baek JH
Shin TI
Shin JH
Oh JW
Kim KP
You Y
Kang EJ
Source :
Organic letters [Org Lett] 2016 Oct 07; Vol. 18 (19), pp. 4900-4903. Date of Electronic Publication: 2016 Sep 27.
Publication Year :
2016

Abstract

An electron-transfer strategy using low-valent iron pentacarbonyl [Fe(CO) <subscript>5</subscript> ] 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) <subscript>5</subscript> , 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.

Details

Language :
English
ISSN :
1523-7052
Volume :
18
Issue :
19
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
27670364
Full Text :
https://doi.org/10.1021/acs.orglett.6b02375