Biocatalytic Strategies for Nitration Reactions
Xiling Wang1, Matteo Aleotti2, Mélanie Hall2,3
1Key Laboratory of Photoelectric Conversion and Utilization of Solar Energy, Qingdao New Energy Shandong Laboratory, CAS Key Laboratory of Biofuels, Shandong Provincial Key Laboratory of Synthetic Biology, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China.
Abstract:
Nitro compounds are key synthetic intermediates used as enabling tools in synthesis and found in a large range of essential compounds, including pharmaceuticals, pesticides, and various organic dyes. Despite recent methodological developments, the industrial preparation of nitro compounds still suffers from harsh reaction conditions, along with poor selectivity and a problematic environmental footprint. Although biological enzymatic methods exist, mild approaches for bionitration are still underexplored. Enzymes, with their exquisite selectivity and compatibility with mild reaction conditions, have the potential to revolutionize the way nitro compounds are prepared. In this perspective, we systematically analyze currently available biological/enzymatic methods, including the oxidation of an amine precursor or methods consisting of direct oxidative nitration and non-oxidative nitration. By examining both the scope and mechanism of these reactions, we aim to present an update on the state-of-the-art while highlighting current challenges in this emerging field. The goal of this perspective is to inspire innovation in enzymatic nitration for sustainable organic synthesis, providing chemists with a valuable guide.
Related Concept Videos
Electrophilic Aromatic Substitution: Nitration of Benzene
Nitriles to Carboxylic Acids: Hydrolysis
Preparation of Amines: Reduction of Oximes and Nitro Compounds
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
Preparation of Nitriles
Rate-Determining Steps
In a multistep reaction mechanism, one of the elementary steps progresses significantly slower than the others. This slowest step is called the rate-limiting step (or rate-determining step). A reaction cannot proceed faster than its slowest step, and hence, the rate-determining step limits the overall reaction rate.
The concept of rate-determining step can be understood from the analogy of a 4-lane freeway with a short-stretch of traffic-bottleneck caused due to...
Nitrosation of Enols


