947232-07-7Relevant academic research and scientific papers
Palladium-Catalyzed Domino Cyclization/Phosphorylation of gem-Dibromoolefins with P(O)H Compounds: Synthesis of Phosphorylated Heteroaromatics
Chen, Chen,Ding, Jie,Liu, Liying,Huang, Yujie,Zhu, Bolin
supporting information, p. 200 - 205 (2021/10/29)
We presented a palladium-catalyzed domino cyclization/phosphorylation of gem-dibromoolefins, which utilize H-phosphinates and secondary phosphine oxides as the phosphine sources, respectively. A variety of phosphorylated heteroaromatics were obtained in m
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.
Copper-catalyzed synthesis of 1-(2-benzofuryl)-N-heteroarenes fromo-hydroxy-gem-(dibromovinyl)benzenes and N-heteroarenes
Rao, Maddali L. N.,Islam, Sk Shamim
supporting information, p. 9076 - 9080 (2021/11/04)
An efficient method for the synthesis of 1-(2-benzofuryl)-N-heteroarenes is developed fromo-hydroxy-gem-(dibromovinyl)benzenes and N-heteroarenes under copper-catalyzed tandem reaction conditions. This methodology displayed a broad substrate scope and high yields in the preparation of a variety of 1-(2-benzofuryl)-N-heteroarenes. Further, 1-(2-benzofuryl)-N-heteroarenes were also applied in the synthesis of polycyclic benzofuro-indolo-pyridine scaffolds under palladium-catalyzed dehydrogenative coupling conditions. Overall, the present tandem approach is general, synthetically advantageous and avoids air-sensitive reagents.
Rapid Access to Benzofuran-Based Natural Products through a Concise Synthetic Strategy
Rao, Maddali L. N.,Murty, Venneti N.
, p. 2177 - 2186 (2016/05/09)
A concise strategy is described for the synthesis of ailanthoidol (1), egonol (2), homoegonol (3), demethoxyegonol (4), demethoxyhomoegonol (5), and stemofuran A (6). This approach involves a Pd-catalysed domino cyclization/coupling process using triarylbismuth reagents for the generation of the benzofuran core. Subsequent structural modifications then give the final targets. The high yielding synthesis of the recently isolated natural products egonol-9(Z)-12(Z)-linoleate (2a), 7-demethoxyegonol-9(Z)-12(Z)-linoleate (4a), and 7-demethoxy-egonol-9(Z)-oleate (4b) are also reported.
Intramolecular cross-coupling of gem-dibromoolefins: A mild approach to 2-bromo benzofused heterocycles
Newman, Stephen G.,Aureggi, Valentina,Bryan, Christopher S.,Lautens, Mark
supporting information; experimental part, p. 5236 - 5238 (2010/01/31)
Highly useful halogenated benzofurans and benzothiophenes are prepared from readily available gem-dibromoolefins using a mild, ligand-free copper catalyzed cross-coupling procedure.
A general and practical method of alkynyl indole and benzofuran synthesis via tandem Cu- And Pd-catalyzed cross-couplings
Nagamochi, Masatoshi,Fang, Yuan-Qing,Lautens, Mark
, p. 2955 - 2958 (2008/02/11)
A new tandem coupling approach to synthesize 2-alkynyl indoles and benzofurans is described. This reaction utilizes easily accessible gemdibromovinyl substrates and terminal alkynes and proceeds via Pd/C- and Cul-catalyzed tandem Ullman/Sonogashira coupli
2-VINYL INDOLES, PYRIDO AND AZEPINO INDOLE DERIVATIVES, 2-ALKYNYL INDOLES, 2-ALKYNYL BENZO[b]FURANS, THEIR PRECURSORS AND NOVEL PROCESSES FOR THE PREPARATION THEREOF
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Page/Page column 89; 150-151, (2008/06/13)
The present invention relates to the preparation of 2-vinyl indoles from ortho-gem-dibromovinylaniline compounds and alkene reagents using a palladium pre-catalyst, a base, and, in some instances, a ligand or additive. The present invention also relates t
