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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.
- 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