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Updated: Jan 10, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Palladium-Catalyzed Denitrogenative Suzuki Coupling of Benzothiatriazine Dioxides for Bi(hetero)aryl-2-sulfonamides
Shigang Wu1, Xiangge Yan1, Wenbin Ding1
1School of Chemistry & Molecular Engineering, East China University of Science & Technology, 130 Meilong Rd, Shanghai 200237, P. R. China.
Abstract:
A palladium-catalyzed denitrogenative Suzuki coupling of N-alkyl benzothiatriazine dioxides with (hetero)aryl boronic acids as well as potassium trifluoroborates is reported, affording a variety of 1,1'-bi(hetero)aryl-2-sulfonamides in yields up to 99% using as low as 0.2 mol % PdCl2(PPh3)2/2PPh3 catalyst in weakly basic aqueous toluene. The protocol shows functional group compatibility as good as the traditional Suzuki coupling. Remarkable steric and electronic effects have been observed from both benzothiatriazine and boron counterparts but could be alleviated by increasing the catalyst loadings alone or in combination with methanol cosolvent. Applications of the protocol have been preliminarily demonstrated in a gram-scale synthesis of κ-opioid receptor antagonist PF-4455242.
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