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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 28期

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

页码：6942 / 6946

页数：5

共 65 条

[11] ORGANOSILANES AS RADICAL-BASED REDUCING AGENTS IN SYNTHESIS
CHATGILIALOGLU, C
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (04) : 188 - 194
[12] Chatgilialoglu C., 2012, Encyclopedia of Radicals in Chemistry Biology and Materials, V1
[13] Chatgilialoglu C., 2001, RADICALS ORGANIC SYN, V1, P28
[14] A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis
Chen, Mark S.
White, M. Christina
[J]. SCIENCE, 2007, 318 (5851) : 783 - 787
[15] Cuerva J. M., 2006, ANGEW CHEM, V118, P5648, DOI DOI 10.1002/ANGE.200600831
[16] Water:: The ideal hydrogen-atom source in free-radical chemistry mediated by TiIII and other single-electron-transfer metals?
Cuerva, Juan M.
Campana, Araceli G.
Justicia, Jose
Rosales, Antonio
Oller-Lopez, Juan L.
Robles, Rafael
Cardenas, Diego J.
Bunuel, Elena
Oltra, J. Enrique
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (33) : 5522 - 5526
[17] Electrogenerated nickel(I) complexes as catalysts for the intramolecular radical cyclisation of unsaturated α-bromoesters
Duñach, E
Esteves, AP
Medeiros, MJ
Olivero, S
[J]. TETRAHEDRON LETTERS, 2004, 45 (42) : 7935 - 7937
[18] Carbon-carbon bond formation with electrogenerated nickel and palladium complexes
Duñach, E
Franco, D
Olivero, S
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (09) : 1605 - 1622
[19] Preparation, structure, and reactivity of nonstabilized organoiron compounds.: Implications for iron-catalyzed cross coupling reactions
Fuerstner, Alois
Martin, Ruben
Krause, Helga
Seidel, Guenter
Goddard, Richard
Lehmann, Christian W.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) : 8773 - 8787
[20] From Oblivion into the Limelight: Iron (Domino) Catalysis
Fuerstner, Alois
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (08) : 1364 - 1367

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