Copper-Catalyzed 8‑Aminoquinoline-Directed Oxidative C–H/N–H Coupling for N‑Arylation of Sulfoximines

A copper-catalyzed cross-dehydrogenative C–H/N–H coupling has been devised to access a series of N-arylated sulfoximines in high yield from 8-aminoquinoline-derived benzamides and sulfoximines. The reaction is scalable, and mechanistic studies favor the involvement of an organometallic pathway, wher...

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Veröffentlicht in:Organic letters 2020-04, Vol.22 (7), p.2606-2610
Hauptverfasser: Grandhi, Gowri Sankar, Dana, Suman, Mandal, Anup, Baidya, Mahiuddin
Format: Artikel
Sprache:eng
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Zusammenfassung:A copper-catalyzed cross-dehydrogenative C–H/N–H coupling has been devised to access a series of N-arylated sulfoximines in high yield from 8-aminoquinoline-derived benzamides and sulfoximines. The reaction is scalable, and mechanistic studies favor the involvement of an organometallic pathway, where C–H bond cleavage is presumed to be the kinetically relevant step. The utility of sulfoximine-coupled benzamides was displayed through the nickel-catalyzed acceptorless dehydrogenative olefination of benzyl alcohols.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00545