Thiophen-2- and -3-carboxylic acid are rapidly and regioselectively metallated by lithium di-isopropy liamide in tetrahydrofuran at –78 °C. The resulting dianionic species [(10) and (4), respectively] react with a range of electrophiles to give the expected thiophencarboxylic acid homologues in good-to-excellent yields.
D. W. Knight and A. P. Nott, J. Chem. Soc., Perkin Trans. 1, 1983, 791 DOI: 10.1039/P19830000791
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