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Catalytic Transfer Hydogenation Reactions for Undergraduate Practical Programs

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R. W. Hanson

Department of Environmental Sciences, University of Plymouth, Plymouth, Devon PL4 8AA, UK

J. Chem. Educ., 1997, 74 (4), p 430

DOI: 10.1021/ed074p430

Publication Date (Web): April 1, 1997

Section:

History, Education, and Documentation

Abstract

A brief review of catalytic transfer hydrogenation (CTH) reactions is given. Attention is drawn, particularly, to the utility of ammonium formate as the hydrogen donor in this type of reaction.

The reduction of aryl carbonyl compounds to the corresponding methylene derivatives by ammonium formate in the presence of 10% Pd/C at 110Â°C is compared to their reductive ammonation which occurs at higher temperatures in the absence of the catalyst (the Leuckart reaction).

It is suggested that the low cost and simplicity of CTH reactions using ammonium formate as the hydrogen donor, together with the high yields obtained in many cases, make them excellent candidates for inclusion in undergraduate practical programmes. Laboratory instructions are given for the reduction of nitrobenzene to aniline (isolated as benzanilide), benzophenone to diphenylmethanol and fluorenone to fluorene, in all cases using ammonium formate as the hydrogen donor and 10% Pd/C as the catalyst. Thin layer chromatography shows that in each case the product is homogeneous; the yields are essentially quantitative.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Catalysis

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