Related Experiment Video
Updated: Nov 8, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Biomimetic Carbene Cascades Enabled Imine Derivative Migration from Carbene-Bearing Thiocarbamates
Xue Li1, Haohua Chen2, Qingqing Xuan1
1Institute of Next Generation Matter Transformation, College of Chemical Engineering and College of Material Sciences Engineering at Huaqiao University, 668 Jimei Boulevard, Xiamen, Fujian 361021, P. R. China.
Abstract:
Inspired by the body circulation of Omeprazole (irreversible proton pump inhibitor), we disclose the carbene-triggered cascades for the synthesis of 2-aminobenzofuran derivatives from N-sulfonyl-1,2,3-triazoles or benzothioazole-bearing thiocarbamates, which represents an unprecedented imine derivative migration process. Furthermore, the desulfurizing reagent-free Barton-Kellogg-type reactions starting from N-sulfonyl-1,2,3-triazoles have also been achieved for the first time, and elemental sulfur is confirmed as a byproduct during this transformation. Both experimental data and DFT calculations further thoroughly explained the unique reactivity.
More Related Videos
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Carbocations
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Cycloaddition Reactions: MO Requirements for Thermal Activation

