91703-34-3

Upstream product

• 90585-32-3 1,1-dibromo-2-(2-methoxyphenyl)ethene 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 42867-45-8 (dibromomethylene)triphenylphosphorane 
• 90-02-8 salicylaldehyde 
• 135-02-4 ortho-anisaldehyde 
• 558-13-4 carbon tetrabromide 

Downstream Products

• 271-89-6 1-benzofurane 
• 5101-44-0 2-ethynyl-phenol 
• 54008-77-4 2-bromo-1-benzofuran 
• 25664-48-6 2-p-tolyl-benzofuran 
• 613-33-2 (4,4'-dimethyl-1,1'-biphenyl) 
• 19234-04-9 2-(p-methoxyphenyl)-benzo[b]furan 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 7168-54-9 4,4'-diethoxybiphenyl 
• 1374787-32-2 2-(4-ethoxyphenyl)benzofuran 
• 1448817-98-8 2-(4-isopropoxyphenyl)benzofuran 
• 128836-59-9 4,4'-Diisopropoxy-biphenyl 
• 39195-66-9 2-(4-chlorophenyl)benzofuran 
• 2050-68-2 4,4'-dichlorobiphenyl 
• 69976-38-1 2-(4-fluorophenyl)benzofuran 

Relevant academic research and scientific papers

Palladium-Catalyzed Domino Cyclization/Phosphorylation of gem-Dibromoolefins with P(O)H Compounds: Synthesis of Phosphorylated Heteroaromatics

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

Copper-catalyzed synthesis of 1-(2-benzofuryl)-N-heteroarenes fromo-hydroxy-gem-(dibromovinyl)benzenes and N-heteroarenes

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.

Highly Efficient Synthesis of 2-Substituted Benzo[ b ]furan Derivatives from the Cross-Coupling Reactions of 2-Halobenzo[ b ]furans with Organoalane Reagents

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.

Synthesis of Diversely Functionalized 2 H-Chromenes through Pd-Catalyzed Cascade Reactions of 1,1-Dibromoolefin Derivatives with Arylboronic Acids

In this work, an unprecedented synthesis of (2H-chromen-2-ylidene)acetates and (2H-chromen-2-ylidene)ethanones with controlled stereoselectivity via Pd-catalyzed cascade reactions of 3-(2-(2,2-dibromovinyl)phenoxy)acrylates or 3-(2-(2,2-dibromovinyl)pheno

Rapid Access to Benzofuran-Based Natural Products through a Concise Synthetic Strategy

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.

Asymmetric hydrogenation of furans and benzofurans with iridium-pyridine-phosphinite catalysts

Enantioselective hydrogenation of furans and benzofurans remains a challenging task. We report the hydrogenation of 2- and 3-substituted furans by using iridium catalysts that bear bicyclic pyridine-phosphinite ligands. Excellent enantioselectivities and high conversions were obtained for monosubstituted furans with a 3-alkyl or 3-aryl group. Furans substituted at the 2-position and 2,4-disubstituted furans proved to be more difficult substrates. The best results (80-97% conversion, 65-82% enantiomeric excess) were obtained with monosubstituted 2-alkylfurans and 2-[4-(trifluoromethyl)phenyl]furan. Benzofurans with an alkyl substituent at the 2- or 3-position also gave high conversions and enantioselectivity, whereas 2-aryl derivatives showed essentially no reactivity. The asymmetric hydrogenation of a 3-methylbenzofuran derivative was used as a key step in the formal total synthesis of the cytotoxic naphthoquinone natural product (-)-thespesone.

Modulators of methyl modifying enzymes, compositions and uses thereof

Agents for modulating methyl modifying enzymes, compositions and uses thereof are provided herein.

Aldehyde-Assisted Ruthenium(II)-Catalyzed C-H Oxygenations

Versatile ruthenium(II) complexes allow for site-selective C-H oxygenations with weakly-coordinating aldehydes. The challenging C-H functionalizations proceed with high chemoselectivity by rate-determining C-H metalation. The new method features an ample substrate scope, which sets the stage for the step-economical preparation of various bioactive heterocycles.

MODULATORS OF METHYL MODIFYING ENZYMES, COMPOSITIONS AND USES THEREOF

Agents for modulating methyl modifying enzymes, compositions and uses thereof are provided herein

Intramolecular cross-coupling of gem-dibromoolefins: A mild approach to 2-bromo benzofused heterocycles

Highly useful halogenated benzofurans and benzothiophenes are prepared from readily available gem-dibromoolefins using a mild, ligand-free copper catalyzed cross-coupling procedure.