Abstract
A generally applicable method for the direct 3-N-arylation of flavins using arylboronic
acids and copper acetate was developed. The reaction conditions were optimized considering
the lability of flavins in basic conditions and thermal heating. Donor- and acceptor-substituted
arylboronic acids were used yielding 3-N-arylflavins in moderate to good yields by
C(aryl)-N(imide) bond formation. UV and fluorescence measurements indicate an orthogonal
orientation of the additional aromatic substituent to the flavin ring system. The
arene substituent is not electronically coupled to the flavin π-system in the ground
state, but electron-rich arene substituents in 3-N position significantly reduce the
flavin emission intensity.
Key words
flavin - N-arylation - boronic acid - isoalloxazin - microwave - copper catalysis
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