Copper-Catalyzed Double Decarboxylative Coupling Reactions of Alkynyl Carboxylic Acid and Glyoxylic Acid: Synthesis of Propargyl Amines and Imidazopyridines

The reaction of alkynyl carboxylic acids, glyoxylic acid derivatives, and amines in the presence of a copper catalyst afforded the corresponding propargyl amines in good yields. The alkynyl carboxylic acid of this coupling reaction shows similar reactivity to that of a terminal alkyne, and the react...

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Published in:Asian journal of organic chemistry 2016-06, Vol.5 (6), p.770-777
Main Authors: Choi, Jinseop, Lim, Jeongah, Irudayanathan, Francis Mariaraj, Kim, Han-Sung, Park, Jaerim, Yu, Su Been, Jang, Yuna, Raja, Gabriel Charles Edwin, Nam, Kye Chun, Kim, Jimin, Lee, Sunwoo
Format: Article
Language:English
Subjects:
Acids
alkynes
Chemical industry
copper
C−C coupling
decarboxylation
multicomponent reactions
Organic chemistry
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Summary:The reaction of alkynyl carboxylic acids, glyoxylic acid derivatives, and amines in the presence of a copper catalyst afforded the corresponding propargyl amines in good yields. The alkynyl carboxylic acid of this coupling reaction shows similar reactivity to that of a terminal alkyne, and the reactivity of the glyoxylic acid is almost identical to that of an aldehyde. When 2‐aminopyridine was employed as the amine source, imidazopyridine derivatives were formed in good yields. It takes al‐kynes: Alkynyl carboxylic acids, phenylglyoxylic acid, and amines in the presence of a copper catalyst afforded propargyl amines in good yields. In this coupling reaction, the alkynyl carboxylic acid has similar reactivity to that of a terminal alkyne, and the reactivity of the glyoxylic acid is almost identical to that of an aldehyde. When 2‐aminopyridine was employed as the amine source, imidazopyridines were formed in good yields.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201600109