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A method for the Cu‐catalyzed, intramolecular dehydrogenative cross‐coupling of 3‐substituted and 3,4‐disubstituted pyrrole–azole systems was developed. The C–H bond in the C2 position was site‐selectively activated over the C–H bond in the C5 position of unsymmetrically substituted pyrroles, and the six‐ and seven‐membered annulated pyrrole products were directly accessed in moderate to good yields.
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