Homogeneous electro-mediated reduction of unsaturated compounds using Ni and Fe as mediators in DMF

阅读量:

47

作者:

APD SilvaSDC MotaLW BieberM Navarro

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摘要:

The homogeneous electro-mediated reduction (HEMR) of several organic compounds (cyclohexene, cyclohexanone, acetophenone, benzaldehyde, styrene, linalool, 1,3-cyclohexadiene, citral, trans-4-phenyl-3-buten-2-one, and piperine) was carried out using Fe 2+, Ni 2+, and [Ni II(bpy)]Br 2 (bpy=2,2′-bipyridine) as electron mediators. An electrochemical system composed of sacrificial anode (Fe, Ni or Zn), nickel cathode, NaI (0.2 M) as supporting electrolyte in DMF and an undivided cell, was used. A constant current ≤100 mA was applied with a maximum cell potential of 2.0 V. Non-conjugated olefins are not reactive, but ketones may be easily reduced to the respective alcohol. In the case of conjugated olefins and ketones, [Ni II(bpy)]Br 2 or Ni 2+ mediator presented good reactivity and selectivity in most cases. Fe 2+ more efficiently mediates the reduction of carbonyl containing systems. Preliminary electroanalytical studies indicate the complexation of the organic substrate by Fe 2+ and Ni 2+ ions and [Ni II(bpy)]Br 2 complex.

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DOI:

10.1016/j.tet.2006.03.067

被引量:

20

年份:

2006

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来源期刊

Tetrahedron
5 June 2006

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2007
被引量:6

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