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Thiocarbamate-Directed Tandem Olefination–Intramolecular Sulfuration of Two Ortho C–H Bonds: Application to Synthesis of a COX‑2 Inhibitor

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journal contribution
posted on 08.02.2018, 16:31 by Wendong Li, Yingwei Zhao, Shaoyu Mai, Qiuling Song
A palladium-catalyzed dual ortho C–H bond activation of aryl thiocarbamates is developed. This tandem reaction initiates by thiocarbamate-directed ortho C–H palladation, which leads to favorable olefin insertion rather than reductive elimination. The oxidative Heck reaction followed by another C–H activation and sulfuration affords the dual-functionalized products. This reaction provides a concise route to the S,O,C multisubstituted benzene skeleton which could be successfully applied for the synthesis of a COX-2 inhibitor.