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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
Copper-Catalyzed Sulfinyl Cross-Coupling Reaction of Sulfinamides
Mengting Kou1, Ziqiang Wei1, Zhen Li1
1Department of Chemistry, Affiliated Nantong Hospital of Shanghai University (The Sixth People's Hospital of Nantong), Shanghai Engineering Research Center of Organ Repair, Innovative Drug Research Center, School of Medicine, Shanghai University, Shanghai 200444, China.
Abstract:
A copper-catalyzed sulfinyl cross-coupling reaction of sulfinamides with aldehyde-derived N-tosylhydrazones is described. This approach enables facile access for the construction of structurally diverse sulfoxides via novel and efficient S-N/S-C bond interconversions, features broad substrate scope, and accommodates various functional groups as well as pharmacophores. Moreover, the given sulfinyl cross-coupling reaction could be scaled up to the gram scale and carried out in a one-pot fashion directly from aldehydes. The broad utility of produced sulfoxides is demonstrated by further transformations. A preliminary mechanistic investigation was performed, which disclosed possible reaction pathways.
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