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Hetero(arene) (0.25 mmol), PhOTf (0.5 mmol), TMPLi (1.0 mmol), −78 °C, 12 h; then CuCN·2LiCl followed by electrophile or O2. Yields are isolated yields. Please see Supporting Information for details.
1,3-C6H4Cl2/PhOTf = 4; 4.8/1 ratio of product/2,2′,6,6′-tetrachlorobiphenyl.
PhCl as benzyne source; n-butylthiophene/PhCl = 1/1; 4.3/1 ratio of product/butylthiophene dimer.
