Metal-Free Mediated Meerwein-Type Reaction: A Radical Cascade Arylation/Aryl Migration/Desulfonylation of Conjugated Alkenes

Metal-Free Mediated Meerwein-Type Reaction: A Radical Cascade Arylation/Aryl Migration/Desulfonylation of Conjugated Alkenes

A metal-free cascade arylation/aryl migration/desulfonylation of N-phenyl-N-(phenylsulfonyl)­meth­acryl­amide is described. The in situ generated diazonium salts from anilines and t-BuONO are used as aryl precursors. This process provides an efficient strategy for the synthesis of α-all-carbon quate...

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Veröffentlicht in:Organic letters 2016-06, Vol.18 (11), p.2612-2615
Hauptverfasser: Ni, Zhangqin, Huang, Xin, Pan, Yuanjiang
Format: Artikel
Sprache:eng
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Zusammenfassung:A metal-free cascade arylation/aryl migration/desulfonylation of N-phenyl-N-(phenylsulfonyl)­meth­acryl­amide is described. The in situ generated diazonium salts from anilines and t-BuONO are used as aryl precursors. This process provides an efficient strategy for the synthesis of α-all-carbon quaternary stereocenters amides. A radical mechanism was proposed for this transformation.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01041