Dedication
The University of Connecticut Holster Scholars Program and Honors Program are thanked
for funding.
Abstract
A methodology is reported for the synthesis of substituted 1,3,5-cycloheptatrienes
by means of an electrocatalytic, aminoxyl-mediated C–N coupling. The reaction employs
commercially available electrodes and standard electrochemical equipment, proceeding
under mild conditions without the need for excess cycloheptatriene, prefunctionalized
starting materials, or added bases. The method is effective across a broad range of
azole substrates, delivering good to excellent product yields. Selectivity is high
and both dimer and by-product formation are effectively suppressed. Operational simplicity,
short reaction times, and scalability make this strategy a practical and versatile
tool for accessing cycloheptatriene derivatives and expanding the scope of electrocatalytic
C–H functionalization reactions.
Keywords
Electrochemistry - C–H functionalization - Azoles - Cycloheptatriene - Nitroxide -
Electrocatalytic
