Iron-Catalyzed Reductive Radical Cyclization of Organic Halides in the Presence of NaBH4: Evidence of an Active Hydrido Iron(I) Catalyst

被引:48
作者
Ekomie, Audrey [1 ]
Lefevre, Guillaume [2 ]
Fensterbank, Louis [1 ]
Lacote, Emmanuel [1 ,3 ]
Malacria, Max [1 ]
Ollivier, Cyril [1 ]
Jutand, Anny [2 ]
机构
[1] Sorbonne Univ, UPMC Univ Paris 06, Inst Parisien Chim Mol, CNRS,UMR 7201, F-75005 Paris, France
[2] UPMC, Ecole Normale Super, Dept Chem, CNRS,ENS,UMR 8640, F-75231 Paris 5, France
[3] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
catalysis; electrochemistry; hydrides; iron; radical reactions; HETEROCYCLIC CARBENE BORANES; SODIUM-BOROHYDRIDE; COUPLING REACTIONS; AROMATIC HALIDES; BOND FORMATION; REAGENT; CHLORIDE; COMPLEXES; HYDROGEN; METALS;
D O I
10.1002/anie.201200589
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Iron made'em: Iron(II) complexes such as FeCl 2 and [FeCl 2(dppe) 2] (dppe=1,2-bisdiphenylphosphinoethane) are efficient precatalysts for the radical cyclization of unsaturated iodides and bromides in the presence of NaBH 4 (see scheme). Cyclic voltammetry studies suggests that the reaction occurs through a radical mechanism via an anionic hydrido iron(I) species as the key intermediate for the activation of the substrates by electron transfer. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:6942 / 6946
页数:5
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