While 3-methyl-thiophene gave both 2-zincated and 5-zincated products (in 16% and 55% yield, respectively), the bulkier 3-phenyl derivative produced only the single isomer shown. The more nucleophilic thiophene 3,4ethylenedioxy-thiophene underwent faster C-H zincation and gave 3e in 72% yield within 1 h. 2,2′-Bithiophene and thiophene also underwent regioselective  C-H zincation to form 3f and 3g in good yield. This zincation methodology also could be applied to furans to provide C-H zincation products 3h-3i in moderate yield, with unreacted starting material making up the mass balance. Pleasingly, even the significantly less activated heteroarenes 2-Br-thiophene and benzothiophene (Mayr N value = -2.6) were amenable, although C-H zincation required a higher temperature for good conversion to 3j and 3k. Note, the benzothiophene C2 and C3 positions have similar reactivity in SEAr, with C2 substitution leading to the thermodynamic product (note, an analogous outcome was observed in electrophilic C-H borylation). Attempts to C-H zincate N-Me-pyrrole and N-Me-indole did appear to proceed, however, conversions were always < 40% and sufficiently clean samples to permit unambiguous characterization of the products could not be obtained.