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Updated: Sep 22, 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
Rhodium(II)-Catalyzed Highly Selective 1,3-Insertion Reactions Using N-Sulfonyl-1,2,3-Triazoles with Heteroaryl
Ga Young Kook1, Daegeun Kim1, Min Ki Chae1
1Department of Chemistry, Wonkwang University, 460 Iksandae-ro, Iksan, Jeonbuk 54538, Republic of Korea.
Abstract:
The transformation of N-sulfonyl-1,2,3-triazoles via insertion/rearrangement is achieved using 2-hydroxybenzimidazole or 2-alkoxybenzothiazole over 3 mol % Rh2(Oct)4 for the synthesis of α-((1H-benzo[d]imidazol-2-yl)amino) ketones or (Z)-2-alkoxy-2-phenylethenamines. This regio- and stereoselective reaction proceeds under mild conditions, is tolerant of functional groups, and has a broad substrate scope. Notably, while the general rhodium-catalyzed reaction involves sigmatropic rearrangement from an allyl vinyl ether, the present synthetic methodology prevents rearrangement owing to the benzimidazole group, allowing access to (Z)-olefins.
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