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Silver-mediated Room Temperature Reactions for the Synthesis of N-α-Ketoacyl Sulfoximines and N-α,β-Unsaturated Acyl Sulfoximines.

ABSTRACT: Here, we report a silver-mediated coupling of acetylenes with sulfoximines to synthesize N-α-ketoacyl sulfoximines and N-α,β-unsaturated acyl sulfoximines. The reactions are performed under an open atmosphere using the oxidant K₂S₂O₈ and the ligand 2,2-bipyridyl. However, the fate of the product formation is controlled by the type of substrate used. The coupling between aryl acetylenes and sulfoximines afforded the N-α-ketoacylsulfoximines, while the alkyl acetylenes provided the N-α,β-unsaturated acyl sulfoximines. Controlled experiments reveal the differential reactivity patterns of substrates. The labeling ¹⁸O experiments showed that water is the source of the incoming oxygen atom for the keto group of N-α-ketoacyl sulfoximines and N-α,β-unsaturated acyl sulfoximines.

SUBMITTER: Gupta R

PROVIDER: S-EPMC9893487 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature

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Silver-mediated Room Temperature Reactions for the Synthesis of N-α-Ketoacyl Sulfoximines and N-α,β-Unsaturated Acyl Sulfoximines.

Gupta Ria R Ahmed Riyaz R Akhter Zaheen Z Kumar Mukesh M Singh Parvinder Pal PP

ACS omega 20230118 4

Here, we report a silver-mediated coupling of acetylenes with sulfoximines to synthesize N-α-ketoacyl sulfoximines and N-α,β-unsaturated acyl sulfoximines. The reactions are performed under an open atmosphere using the oxidant K2S2O8 and the ligand 2,2-bipyridyl. However, the fate of the product formation is controlled by the type of substrate used. The coupling between aryl acetylenes and sulfoximines afforded the N-α-ketoacylsulfoximines, w ...[more]

PMID: 36743040

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