Attenberger, B. and Schmaderer, H. and König, B. (2008) Copper-mediated 3-N-Arylation of Flavin. Synthesis 11, 1767 - 1774.
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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.
|Institutions:||Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König|
|Projects:||GRK 640 Sensory photoreceptors in natural and artificial systems|
|Keywords:||flavin, N-arylation, boronic acid, isoalloxazin, microwave, copper catalysis|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Yes|
|Deposited On:||05 Mar 2009 11:55|
|Last Modified:||27 Aug 2012 15:05|
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