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![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Copper-Catalyzed Synthesis of Thiadiazine-1-oxides in Reusable Aqueous Medium under External [Ag]/Ligand/Base-Free
Cui Wu1, Riting Huang1, Ming Zhang1
1Key Laboratory of Functional Small Organic Molecules, Ministry of Education, and College of Chemistry and Chemical Engineering , Jiangxi Normal University , 99 Ziyang Road , Nanchang , Jiangxi 330022 P. R. China.
Abstract:
We report herein a copper-catalyzed multicomponent reaction of simple NH-sulfoximine with readily available aldehyde and TMSN3 in hot water and aerobic conditions. The reaction tolerated a broad range of functional groups under external [Ag]/ligand/base-free conditions and can form three C-N bonds in a one-pot transformation, thus representing an extremely cost-effective protocol to biologically active sulfoximine derivatives. This aqueous catalytic system could be circularly utilized in consecutive runs of gram-scale preparations of thiadiazine-1-oxides without extra addition of the copper catalyst and PTA. Mechanistically, an ″ortho-binding″ effect in ortho-bromo NH-sulfoximine was proposed to control the chemoselectivity; thus, the other free halides such as bromo- or iodo-atoms in aldehydes 2 were compatible in the reaction.
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