Pd-Catalyzed Decarboxylative Coupling of Propiolic Acids: One-Pot Synthesis of 1,4-Disubstituted 1,3-Diynes via Sonogashira−Homocoupling Sequence

One-pot synthesis of symmetric 1,4-disubstituted 1,3-diynes from iodoarenes and propiolic acid via Sonogashira reaction followed by Pd-catalyzed decarboxylative homocoupling is developed in high yields. Also, this system allows the one-pot synthesis of unsymmetric 1,4-disubstituted 1,3-diynes by cro...

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Bibliographic Details
Published in:Journal of organic chemistry 2011-04, Vol.76 (7), p.2214-2219
Main Authors: Park, Jihye, Park, Eonjeong, Kim, Aejin, Park, Seul-A, Lee, Youngil, Chi, Ki-Whan, Jung, Young Hoon, Kim, In Su
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Catalysis
Chemistry
Combinatorial Chemistry Techniques
Cross-Linking Reagents - chemistry
Diynes - chemical synthesis
Diynes - chemistry
Exact sciences and technology
Magnetic Resonance Spectroscopy
Molecular Structure
Noncondensed benzenic compounds
Organic chemistry
Palladium - chemistry
Preparations and properties
Propionates - chemistry
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Summary:One-pot synthesis of symmetric 1,4-disubstituted 1,3-diynes from iodoarenes and propiolic acid via Sonogashira reaction followed by Pd-catalyzed decarboxylative homocoupling is developed in high yields. Also, this system allows the one-pot synthesis of unsymmetric 1,4-disubstituted 1,3-diynes by cross-coupling of two different 3-substituted propiolic acids.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo200096x