Alkali metal reductions of organic molecules: why mediated electron transfer from lithium is faster than direct reduction.

Journal article

Lithium metal reductions are widely employed in organic synthesis, where it is common to employ a "mediator" to speed up the electron transfer kinetics. We present experimental data for the electrode kinetics of the reduction of the most common mediator, 4,4'-di-tert-butyl-1,1'-biphenyl (DBB) in tetrahydrofuran (THF) over a range of temperatures. Using corresponding data for the oxidation of lithium we present quantitative estimates of the kinetic advantage for the use of DBB as a mediator in lithium reductions, over, in particular, direct reduction using lithium metal.

Authors: Rees, N; Baron, R; Kershaw, N; Donohoe, T; Compton, R

• Publication status: Published
• Journal: Journal of the American Chemical Society
• Volume: 130
• Issue: 37
• Pages: 12256-12257
• Publication date: 2008-09-01
• DOI: 10.1021/ja805086w
• EISSN: 1520-5126
• ISSN: 0002-7863
• Language: English