Sustainability Metric Case Study on Biaryl Bond Formation

Abstract

The most common metric used to measure chemical processes is yield, which does not take into account all inputs. A more holistic view of chemical reactions is needed and a metric based analysis could be used to systematically focus methodological improvements. This project looks at the synthetic efficiency of an industrially relevant bond forming reaction, biaryl formation, and attempts to inventory all inputs used in this reaction. The formation of phenylnaphthalene was studied as a model system to compare carbon-carbon bond formation reactions. The reactions were analyzed based on method, reaction conditions, catalyst composition, reagent loading, and other inputs (energy and solvent). The reactions were classified based on eight possible coupling permutations. The methods included reactions between nucleophilic or electrophilic naphthalene and phenyl derivatives as well as C-H bonds. Via this holistic metric based analysis, reactions with many dissimilar variables will be compared.