1172576-91-8Relevant academic research and scientific papers
Cross-coupling reaction of organoalane reagents with 2-mercaptobenzo-5-membered heterocycles for efficient synthesis of benzo-5-membered heterocycle sulfides
Luo, Rui-Qiang,Guo, Shao Peng,Xiao, Hong-Liu,Li, Qing-Han
, (2021/12/03)
A highly efficient and simple route for the synthesis of benzo-5-membered heterocycles sulfides has been developed by the cross-coupling reaction of 2-mercaptobenzo-5-membered heterocycles with (hetero)arylaluminum reagents. Various benzo-5-membered heter
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.
Ethylaluminum as an ethylene source for the Mizoroki-Heck-type reaction. Rhodium-catalyzed preparation of stilbene derivatives
Tanaka, Shota,Itami, Kazuki,Sunahara, Kazuhiro,Tatsuta, Go,Mori, Atsunori
supporting information, p. 1949 - 1952 (2015/02/05)
Treatment of an organoaluminum reagent bearing aryl and ethyl groups furnishes 1,2-diarylethene derivatives in good to excellent yields by the catalysis of a rhodium complex, in which the ethyl group of the aluminum reagent serves as an ethylene source in the product formation.
Rhodium-Catalyzed Cross-Coupling of Vinylarenes with Arylaluminum Reagents in the Presence of Ketones
Tanaka, Shota,Mori, Atsunori
supporting information, p. 1167 - 1171 (2015/10/05)
Rhodium-catalyzed addition/elimination of arylaluminum reagents with vinylarenes was achieved to obtain stilbene derivatives. The reaction of diethyl(phenyl)aluminum with styrene in the presence of the chloro(1,5-cyclooctadiene)rhodium(I) dimer, [RhCl(cod)]2, and diisopropyl ketone (2,4-dimethyl-3-pentanone) as an additive occurred to give (E)-stilbene in quantitative yield. The use of other arylaluminum reagents afforded β-arylated products in good to excellent yields. This reaction was found to be promoted by ketones as additives, which are reduced to the corresponding alcohols, as confirmed by analysis of the crude reaction mixture by 1H NMR spectroscopy.
Quaternary carbon stereogenic centers through copper-catalyzed enantioselective allylic substitutions with readily accessible aryl- or heteroaryllithium reagents and aluminum chlorides
Gao, Fang,Lee, Yunmi,Mandai, Kyoko,Hoveyda, Amir H.
, p. 8370 - 8374 (2010/12/25)
The case of the notorious aryls is solved: The first efficient catalytic and enantioselective method for allylic substitutions that furnish quaternary carbon stereogenic centers by additions of aryl- or heteroarylmetals is reported (see scheme). Highly site- and enantioselective processes begin with readily available organolithium reagents.
