Rhodium-catalyzed direct C-H bond alkynylation of aryl sulfonamides with bromoalkynes

Organic & Biomolecular Chemistry
Hongcen HouJunmin Chen

Abstract

Herein we report a novel rhodium-catalyzed ortho-mono-alkynylation of aryl sulfonamides. The reactions of N-tosylacetamides with triisopropylsilyl (TIPS)-substituted bromoalkyne are catalyzed by a [(Cp*RhCl2)2] complex without cyclization, forming ortho-(1-alkynyl) benzenesulfonamides. While triethylsilyl or trimethylsilyl (TES or TMS)-substituted bromoalkyne was also amenable to the alkynylation, affording six-membered benzosultams via the alkynylation/intramolecular cyclization cascade reaction. The present protocol displays high functional group tolerance and broad substrate scope under an air atmosphere in good to high yields. Mechanistic studies indicate that the reaction proceeds by a turnover limiting C-H activation step and a plausible mechanism was proposed.

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Citations

Sep 27, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Quan-Qing Zhao, Xiao-Qiang Hu
May 7, 2021·Chemistry, an Asian Journal·Mary Sravani GallaNagula Shankaraiah
May 27, 2021·Chemistry : a European Journal·Karunanidhi MuraliDebabrata Maiti

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