24472-98-8Relevant articles and documents
Highly Efficient Synthesis of 2-Substituted Benzo[ b ]furan Derivatives from the Cross-Coupling Reactions of 2-Halobenzo[ b ]furans with Organoalane Reagents
Wen, Chang,Wu, Chuan,Luo, Ruiqiang,Li, Qinghan,Chen, Feng
supporting information, p. 3847 - 3861 (2021/07/02)
A highly efficient and simple route for the synthesis of 2-substituted benzo[ b ]furans has been developed by palladium-catalyzed cross-coupling reaction of 2-halobenzo[ b ]furans with aryl, alkynyl, and alkylaluminum reagents. Various 2-aryl-, 2-alkynyl-, and 2-alkyl-substituted benzo[ b ]furan derivatives can be obtained in 23-97% isolated yields using 2-3 mol% PdCl 2/4-6 mol% XantPhos as the catalyst under mild reaction conditions. The aryls bearing electron-donating or electron-withdrawing groups in 2-halobenzo[ b ]furans gave products in 40-97% isolated yields. In addition, aluminum reagents containing thienyl, furanyl, trimethylsilanyl, and benzyl groups worked efficiently with 2-halobenzo[ b ]furans as well, and three bioactive molecules with 2-substituted benzo[ b ]furan skeleton were synthesized. Furthermore, the broad substrates scope and the typical maintenance of vigorous efficiency on gram scale make this protocol a potentially practical method to synthesize 2-substituted benzo[ b ]furan derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.
CuI catalyzed domino coupling–cyclization of 2-iodo-phenols and 1-alkynes to the synthesis of 2-substituted benzo[b]furans/furo-pyridines
Chen, Ze-Pin,Zhou, Yi,Shui, Meng-Zhu,Liu, Feng
supporting information, p. 133 - 136 (2018/12/11)
CuI/proline-catalyzed coupling reaction of 2-iodo-phenols with terminal alkynes and the following cyclization process is carried out successively in DMSO at 80 °C. Under this tandem process, 2-substituted benzo[b]furans/furo-pyridines were synthesized in good to excellent yields with a great diversity.
Preparation method of multi-substituted benzofuran derivative
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Paragraph 0027-0029, (2018/05/30)
The invention provides a preparation method of a multi-substituted benzofuran derivative. The multi-substituted benzofuran derivative is obtained by taking end alkyne and a halogenated phenol derivative as starting raw materials, copper salt as a catalyst and amino acid as an additive and performing coupling reaction in an organic solvent under the condition of adding alkali, wherein the catalystis CuX, X is iodine or bromine, the molar ratio of the catalyst to the halogenated phenol derivative is (0.001-0.5):1, the molar ratio of the amino acid to the catalyst is (0.1-3):1, the molar ratio of the halogenated phenol derivative to the end alkyne is (1-1.5):1, and the reaction temperature is 30 to 150 DEG C. An expensive palladium catalyst liable to cause environmental pollution is not used. The method is simple in process and high in operability, and has a good industrial application prospect.
