Rhodium-Catalyzed Alkylation of C–H Bonds in Aromatic Amides with α,β-Unsaturated Esters

The alkylation of C–H bonds with α,β-unsaturated carbonyl compounds by a rhodium-catalyzed reaction of aromatic amides containing an 8-aminoquinoline moiety is reported. The reaction is highly regioselective. The formation of C–C bonds occurs between the ortho C–H bonds in aromatic amides and the β-...

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Veröffentlicht in:Organic letters 2014-10, Vol.16 (19), p.5148-5151
Hauptverfasser: Shibata, Kaname, Chatani, Naoto
Format: Artikel
Sprache:eng
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Zusammenfassung:The alkylation of C–H bonds with α,β-unsaturated carbonyl compounds by a rhodium-catalyzed reaction of aromatic amides containing an 8-aminoquinoline moiety is reported. The reaction is highly regioselective. The formation of C–C bonds occurs between the ortho C–H bonds in aromatic amides and the β-position of the acyclic α,β-unsaturated carbonyl compounds. The reaction is applicable to various acyclic α,β-unsaturated carbonyl compounds, such as acrylic esters, acrylamide, fumarate, maleate, and phenyl vinyl sulfone.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502500c