Synthesis of Isocoumarins via Pd/C-Mediated Reactions of o-Iodobenzoic Acid with Terminal Alkynes

Synthesis of Isocoumarins via Pd/C-Mediated Reactions of o-Iodobenzoic Acid with Terminal Alkynes

The coupling reaction of o-iodobenzoic acid with terminal alkynes by using a catalyst system of 10% Pd/C−Et3N−CuI−PPh3 has been studied in a variety of solvents. 3-Substituted isocoumarins were formed in good yields and with good regioselectivity when the reaction was performed in EtOH.

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Veröffentlicht in:Journal of organic chemistry 2005-06, Vol.70 (12), p.4778-4783
Hauptverfasser: Subramanian, Venkataraman, Batchu, Venkateswara Rao, Barange, Deepak, Pal, Manojit
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Catalysis
Chemistry
Combinatorial Chemistry Techniques
Coumarins - analysis
Coumarins - chemical synthesis
Ethanol - chemistry
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Iodobenzoates - chemistry
Molecular Structure
Organic chemistry
Palladium - chemistry
Preparations and properties
Solvents
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Zusammenfassung:The coupling reaction of o-iodobenzoic acid with terminal alkynes by using a catalyst system of 10% Pd/C−Et3N−CuI−PPh3 has been studied in a variety of solvents. 3-Substituted isocoumarins were formed in good yields and with good regioselectivity when the reaction was performed in EtOH.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo050440e