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

• Published in: Asian journal of organic chemistry Vol. 5; no. 6; pp. 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: Journal Article
• Language: English
• Published: Weinheim Blackwell Publishing Ltd 01-06-2016; Wiley Subscription Services, Inc
• Subjects: Acids; alkynes; Chemical industry; copper; C−C coupling; decarboxylation; multicomponent reactions; Organic chemistry
• ISSN: 2193-5807; 2193-5815
• DOI: 10.1002/ajoc.201600109

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.