Radical Hydrodeiodination of Aryl, Alkenyl, Alkynyl, and Alkyl Iodides with an Alcoholate as Organic Chain Reductant through Electron Catalysis
- 21 April 2016
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition
- Vol. 55 (23) , 6749-6752
Abstract
A simple and efficient method for radical hydrodeiodination is reported. The novel approach uses electron catalysis. In situ generated Na‐alcoholates are introduced as radical chain reducing reagents and reactions work with O2 as cheap initiator. Hydrodeiodination works on aryl, alkenyl, alkynyl iodides and a tert‐alkyl iodide also gets reduced applying the method. Albeit less general, the method is also applicable to the reduction of aryl bromides. The novel reagent is successfully used to conduct typical reductive radical cyclization reactions and mechanistic studies are reported.Keywords
Funding Information
- WWU Münster
This publication has 56 references indexed in Scilit:
- Iron‐Catalyzed Reductive Radical Cyclization of Organic Halides in the Presence of NaBH4: Evidence of an Active Hydrido Iron(I) CatalystAngewandte Chemie, 2012
- Electron Transfer to Benzenes by Photoactivated Neutral Organic Electron Donor MoleculesAngewandte Chemie International Edition, 2012
- Electron Transfer to Benzenes by Photoactivated Neutral Organic Electron Donor MoleculesAngewandte Chemie, 2012
- Cobalt‐Catalyzed Coupling of Alkyl Iodides with Alkenes: Deprotonation of Hydridocobalt Enables TurnoverAngewandte Chemie International Edition, 2011
- Cobalt‐Catalyzed Coupling of Alkyl Iodides with Alkenes: Deprotonation of Hydridocobalt Enables TurnoverAngewandte Chemie, 2011
- Highly Efficient Reduction of Unactivated Aryl and Alkyl Iodides by a Ground‐State Neutral Organic Electron DonorAngewandte Chemie International Edition, 2005
- Selective reduction of organic compounds with aluminum and boron hydridesPure and Applied Chemistry, 1996
- Tri-n-butyltin Hydride as Reagent in Organic SynthesisSynthesis, 1987
- The Hydrogenolysis of Organic HalidesSynthesis, 1980
- Relative reactivities of methanol and methoxide ion as hydrogen atom donors to the p-nitrophenyl radicalJournal of the American Chemical Society, 1974