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

作者: Audrey Ekomié , Guillaume Lefèvre , Louis Fensterbank , Emmanuel Lacôte , Max Malacria

DOI: 10.1002/ANIE.201200589

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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 bromides in presence NaBH(4). Cyclic voltammetry studies suggests that reaction occurs through a mechanism via an anionic hydrido iron(I) species key intermediate activation substrates by electron transfer.

参考文章(54)
E. Duñach, A.P. Esteves, M.J. Medeiros, S. Olivero, Electrogenerated Nickel(I) complexes as catalysts for the intramolecular radical cyclisation of unsaturated α-bromoesters Tetrahedron Letters. ,vol. 45, pp. 7935- 7937 ,(2004) , 10.1016/J.TETLET.2004.08.131
John Hartung, Mary E. Pulling, Deborah M. Smith, David X. Yang, Jack R. Norton, Initiating radical cyclizations by H transfer from transition metals Tetrahedron. ,vol. 64, pp. 11822- 11830 ,(2008) , 10.1016/J.TET.2008.10.030
Shau-Hua Ueng, Malika Makhlouf Brahmi, Étienne Derat, Louis Fensterbank, Emmanuel Lacôte, Max Malacria, Dennis P. Curran, Complexes of Borane and N-Heterocyclic Carbenes: A New Class of Radical Hydrogen Atom Donor Journal of the American Chemical Society. ,vol. 130, pp. 10082- 10083 ,(2008) , 10.1021/JA804150K
Deborah M. Smith, Mary E. Pulling, Jack R. Norton, Tin-Free and Catalytic Radical Cyclizations Journal of the American Chemical Society. ,vol. 129, pp. 770- 771 ,(2007) , 10.1021/JA0673276
Pim-Huat Phua, Laurent Lefort, Jeroen A. F. Boogers, Mar Tristany, Johannes G. de Vries, Soluble iron nanoparticles as cheap and environmentally benign alkene and alkyne hydrogenation catalysts Chemical Communications. ,vol. 40, pp. 3747- 3749 ,(2009) , 10.1039/B820048C
Anny Jutand, Contribution of Electrochemistry to Organometallic Catalysis Chemical Reviews. ,vol. 108, pp. 2300- 2347 ,(2008) , 10.1021/CR068072H
Guillaume Lefèvre, Marc Taillefer, Carlo Adamo, Ilaria Ciofini, Anny Jutand, First Evidence of the Oxidative Addition of Fe0(N,N)2 to Aryl Halides: This Precondition Is Not a Guarantee of Efficient Iron‐Catalysed C–N Cross‐Coupling Reactions European Journal of Organic Chemistry. ,vol. 2011, pp. 3768- 3780 ,(2011) , 10.1002/EJOC.201100454
Ilhyong Ryu, Shohei Uehara, Hidefumi Hirao, Takahide Fukuyama, Tin-free Giese reaction and the related radical carbonylation using alkyl iodides and cyanoborohydrides. Organic Letters. ,vol. 10, pp. 1005- 1008 ,(2008) , 10.1021/OL7031043
Shau-Hua Ueng, Louis Fensterbank, Emmanuel Lacôte, Max Malacria, Dennis P. Curran, Radical deoxygenation of xanthates and related functional groups with new minimalist N-heterocyclic carbene boranes Organic Letters. ,vol. 12, pp. 3002- 3005 ,(2010) , 10.1021/OL101015M