Copper-catalyzed denitrogenative N-arylation of sulfoximines and sulfonamides with arylhydrazines

A Cu-mediated ligand-free arylation of NH-sulfoximines and sulfonamides by arylhydrazine hydrochlorides was herein demonstrated. The oxidative transformation provided an easy access towards N-aryl sulfoximines and sulfonamides in high yields (up to 93% yields) with broad functional groups tolerance...

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Bibliographic Details
Published inTetrahedron Vol. 75; no. 29; pp. 3886 - 3893
Main Authors Dong, Wanrong, Liu, Chaoyang, Ma, Xinchi, Zhang, Yingjun, Peng, Zhihong, Xie, Dexun, An, Delie
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 19.07.2019
Elsevier
Subjects
Arylhydrazines
Chemistry
Chemistry, Organic
Copper catalysis
Dehydrogenative arylation
NH-Sulfoximines
Physical Sciences
Science & Technology
Sulfonamides
Dehydrogenative arylation
NH-Sulfoximines
Arylhydrazines
Sulfonamides
Copper catalysis
PALLADIUM
LIGAND-FREE
BOND FORMATION
ARYLBORONIC ACIDS
ARYL BROMIDES
BORONIC ACIDS
REUSABLE CATALYST
IODIDES
COUPLING REACTION
EFFICIENT
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Summary:A Cu-mediated ligand-free arylation of NH-sulfoximines and sulfonamides by arylhydrazine hydrochlorides was herein demonstrated. The oxidative transformation provided an easy access towards N-aryl sulfoximines and sulfonamides in high yields (up to 93% yields) with broad functional groups tolerance (up to 36 examples). The protocol was proposed to take place through the free radical pathway based on the results of control reactions and EPR analysis. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2019.05.039