In contemporary chemistry, photoredox catalysis has proven to be an important strategy in the synthesis of new compounds. In these reactions, light is absorbed by a photoredox catalyst, which then initiates an electron transfer reaction. Previously published reports of this technique have primarily used ruthenium and iridium photoredox catalysts; unfortunately, these elements are both expensive rare-earth metals. However, potential replacements exist: certain copper complexes show promise in exhibiting similar photophysical properties as more popular photoredox catalysts, and copper is earth-abundant and relatively inexpensive. For these reasons, we have been evaluating bis(phenanthroline) copper(I) derivatives for the catalysis of enantioselective aldehydes α-alkylation, a reaction facilitated by a chiral catalyst to control facial selectivity. In the course of this investigation, a number of copper(I) complexes have been tested under a range of reaction conditions, including varying solvents, light sources, and work-up procedures. Our initial results suggest that ligand substitution has a significant effect on reactant conversion and product yield.  In this presentation, we will present collective data from our trials and describe how yield and enantiomeric excess are affected by the factors listed above.<br/>

Evaluation of copper photoredox catalysts in the synthesis of chiral molecules

251st National Meeting (2016)

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