Biocatalysis

Mechanism + Description

A number of enzymes and whole cell systems are known to reduce nitrobenzenes to anilines. These are often labelled as nitroreductases, but in most cases are probably other redox proteins like ferridoxin / ENE reductases working in a promiscuous fashion. The mechanism probably depends on the enzymes – electron transfer / protonation of delivery of hydride from NAD(P)H

General comments

A potentially green and safe way to produce anilines from nitrobenzenes. A detraction is the very poor throughput compared to chemo-catalyzed processes. Some enzyme systems will only reduce very electron poor nitrobenzenes.

Key references

Enzyme and Microbial Technology 2008, 42, 308 Reduction of aliphatic nitro groups using an obligatory anaerobic whole cell biocatalyst
Tet. Lett, 1997, 38, 3043 baker’s yeast (Saccharomyces Cerevisiae) mediated reduction of nitroarenes

Relevant scale up example

None found.