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2.6.1.1.2.3 Sulfonamide Directing Groups

DOI: 10.1055/sos-SD-218-00088

Zhang, H.; Liu, C.; Lei, A.Science of Synthesis: Catalytic Transformations via C—H Activation, (20152143.

4-Toluenesulfonamide 10 (R1 = Me) undergoes a palladium(II)-catalyzed C—H carboxylation to afford the ortho-carboxylated product 11 (R1 = Me) in moderate yield (Scheme 7).[‌19‌] The sulfonamide is as a powerful directing group in this transformation. Celecoxib analogue 11 [R1 = 5-(4-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl] can also be prepared using the same protocol.

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References


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