Abstract
In situ generated arynes react with nitrile imines derived from trifluoroacetonitrile at 0 °C in THF solutions yielding 3-trifluoromethyl-1H-indazole derivatives as the only intermolecular products. The reaction corresponds the expected (3 + 2)-cycloadditions which belong to the Type III (inverse-electron-demand) of Sustmann’s classification. Subsequent CAN-mediated dearylation of the model N-(p-methoxy)phenyl indazole leads to N-unsubstituted analogue, which easily undergoes alkylation and acylation reactions. Presented protocol offers a superior method for preparation of the 3-CF3 substituted indazole derivatives.
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