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Unexpected CO bond formation in Suzuki coupling of 4‐chlorothieno[2,3‐ d ]pyrimidines
Author(s) -
Perspicace Enrico,
Hesse Stéphanie,
Kirsch Gilbert,
Yemloul Mehdi,
Lecomte Claude
Publication year - 2009
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.107
Subject(s) - chemistry , microwave irradiation , palladium , microwave , suzuki reaction , microwave heating , coupling (piping) , photochemistry , argon , irradiation , organic chemistry , polymer chemistry , medicinal chemistry , catalysis , mechanical engineering , physics , quantum mechanics , nuclear physics , engineering
Palladium‐catalyzed Suzuki reactions were performed on 4‐chlorothieno[2,3‐ d ]pyrimidines under classical heating conditions and under microwave irradiation. Some unexpected results were obtained during this study as two kinds of compounds were isolated depending on the conditions used. A careful investigation of experimental details has shown that the expected CC bond formation occurred when degassed solvents were used (both in classical and microwave heating) whereas an unexpected CO bond formation happened when solvents were not degassed with argon‐bubbling before use. J. Heterocyclic Chem., 46, 459 (2009).