Affiliation:
1. College of Chemistry and Environment, Southwest Minzu University
2. Key Laboratory of General Chemistry of the National Ethnic Affairs Commission, College of Chemistry and Environment, Southwest Minzu University
3. Key Laboratory of Pollution Control Chemistry and Environmental Functional Materials for Qinghai-Tibet Plateau of the National Ethnic Affairs Commission, College of Chemistry and Environment, Southwest Minzu University
Abstract
AbstractA 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% PdCl2/4–6 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.
Funder
Department of Science and Technology Sichuan Province
Southwest Minzu University
Fundamental Research Funds for the Central Universities
Subject
Organic Chemistry,Catalysis
Cited by
3 articles.
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