Direct Functionalization of Indoles: Copper-Catalyzed Malonyl Carbenoid Insertions

Direct Functionalization of Indoles: Copper-Catalyzed Malonyl Carbenoid Insertions

Indoles, when treated with dimethyl diazomalonate under catalysis by Cu(acac)2, undergo C−H insertion reactions regioselectively depending on the substitution pattern on the indole moiety. Indoles where the 3-position is substituted give high yields of the C2−H insertion product. Microwave condition...

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Veröffentlicht in:Organic letters 2010-11, Vol.12 (21), p.4956-4959
Hauptverfasser: Johansen, Michael B, Kerr, Michael A
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Copper - chemistry
Indoles - chemistry
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
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Zusammenfassung:Indoles, when treated with dimethyl diazomalonate under catalysis by Cu(acac)2, undergo C−H insertion reactions regioselectively depending on the substitution pattern on the indole moiety. Indoles where the 3-position is substituted give high yields of the C2−H insertion product. Microwave conditions are also disclosed which show comparable yields with reduced reaction times.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1020948