Jump to main content
Jump to site search

Issue 11, 2019
Previous Article Next Article

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

Author affiliations

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.

Graphical abstract: Rhodium-catalyzed direct C–H bond alkynylation of aryl sulfonamides with bromoalkynes

Back to tab navigation

Supplementary files

Article information


Submitted
10 Jan 2019
Accepted
12 Feb 2019
First published
15 Feb 2019

Org. Biomol. Chem., 2019,17, 2948-2953
Article type
Paper

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

H. Hou, Y. Zhao, S. Pu and J. Chen, Org. Biomol. Chem., 2019, 17, 2948
DOI: 10.1039/C9OB00061E

Social activity

Search articles by author

Spotlight

Advertisements