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Updated: May 15, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Indole-Quinoline Transmutation Enabled by a Formal Rhodium Carbynoid
Lu-Jie Liu1, Meng-Yang Tian1, Zhi-Yu Lang1
1Guizhou Provincial Key Laboratory of Innovation and Manufacturing for Pharmaceuticals, School of Pharmacy, Zunyi Medical University, No. 6 West Xuefu Rd., Zunyi, 563006, China.
Abstract:
Skeleton editing is an emerging and powerful tool in organic chemistry because it can simplify synthetic procedures towards complex molecules. Herein, we present an approach for indole-quinoline transmutation through rhodium-catalyzed single-carbon insertion into the C2(sp2)─C3(sp2) bond of an indole with an α-diazotrifluoroethyl sulfonium salt that we developed. This protocol involves a formal trifluoromethyl rhodium carbynoid (CF3C+ = Rh) resembling a trifluoromethyl cationic carbyne (CF3C+:), allowing facile access to an array of quinolines in moderate to high yields. Potential applications in the late-stage skeletal editing of pharmaceutical and natural product derivatives, preparation of adapalene analogs, scaled-up synthesis, and transformations of products are highlighted. Finally, a computational study was conducted to support the envisioned mechanism.
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