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Synfacts 2011(11): 1223-1223
DOI: 10.1055/s-0031-1289194
DOI: 10.1055/s-0031-1289194
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Pd-Catalyzed Direct Alkynylation of Aliphatic C-H Bonds
Contributor(s):Paul Knochel, Andreas K. SteibY. Ano, M. Tobisu*, N. Chatani*
Osaka University, Suita, Japan
Palladium-Catalyzed Direct Ethynylation of C(sp³)-H Bonds in Aliphatic Carboxylic Acid Derivatives
J. Am. Chem. Soc. 2011, 133: 12984-12986
Osaka University, Suita, Japan
Palladium-Catalyzed Direct Ethynylation of C(sp³)-H Bonds in Aliphatic Carboxylic Acid Derivatives
J. Am. Chem. Soc. 2011, 133: 12984-12986
Further Information
Publication History
Publication Date:
19 October 2011 (online)
Key words
alkynylation - C-H activation - palladium
Significance
The first palladium-catalyzed alkynylation of unactivated C(sp³)-H bonds in aliphatic carboxylic acid derivatives has been disclosed. 8-Aminoquinoline proved to be the best directing group to promote the desired alkynylation reaction.
Comment
Interestingly, replacement of the
8-aminoquinoline
moiety with a 1-aminonaphthyl group or N-methylation of the amide
group completely inhibited the ethynylation reaction, indicating
that both, the nitrogen of the quinoline moiety and the NH group
of the amide are essential for the reaction.