26039-91-8

Upstream product

• 127745-66-8 2-(benzyloxy)-5-(methoxy)acetophenone 
• 17332-11-5 2-bromo-4-methoxyphenol 
• 93-55-0 1-phenyl-propan-1-one 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 447-31-4 Desyl chloride 

Downstream Products

• 76395-97-6 5-hydroxy-3-methyl-2-phenylbenzofuran 
• 1448962-64-8 4-([1,4'-bipiperidin]-1'-ylmethyl)-3-methyl-2-phenylbenzofuran-5-ol 
• 229323-37-9 2-(5-methoxy-2-phenylbenzo[b]furan-3-yl)acetonitrile 
• 29540-37-2 2-(5-methoxy-2-phenylbenzo[b]furan-3-yl)ethylamine 

Relevant academic research and scientific papers

Di-tert-butylneopentylphosphine (DTBNpP): An Efficient Ligand in the Palladium-Catalyzed α-Arylation of Ketones

Di-tert-butylneopentylphosphine (DTBNpP) and palladium(II) acetate provide an efficient catalytic system for the α-arylation of ketones. Aryl bromides were coupled with ketones using 0.25-0.5 mol-% Pd(OAc)2/DTBNpP in toluene at 50 C, whereas aryl chlorides required a higher catalyst loading (0.5-2.0 mol-%) and a higher temperature (80 C). Coupling of 2-bromophenol with ketones using the Pd/DTBNpP system provides an efficient route for the synthesis of benzofurans.

Benzofuran derivatives as anticancer inhibitors of mTOR signaling

A series of 32 derivatives and isosteres of the mTOR inhibitor 2 were synthesized and compared for their cytotoxicity in radioresistant SQ20B cancer cell line. Several of these compounds, in particular 30b, were significantly more cytotoxic than 2. Importantly, 30b was shown to block both mTORC1 and Akt signaling, suggesting insensitivity to the resistance associated to Akt overactivation observed with rapamycin derivatives currently used in clinic.

One-pot synthesis of benzofurans via palladium-catalyzed enolate arylation with o-bromophenols

(Chemical Equation Presented) A one-pot synthesis of benzofurans which utilizes a palladium-catalyzed enolate arylation is described. The process demonstrates broad substrate scope and provides differentially substituted benzofurans in moderate to excelle

Generation of reactive low-valent titanium species using metal-arenes as efficient organic reductants for TiCl3: Applications to organic synthesis

A comprehensive study on the use of metal-arene systems as organic reductants for TiCl3 has resulted in an efficient method for the generation of highly reactive low-valent titanium (LVT) reagents. The activated titanium species could be prepared by refluxing a mixture of substoichiometric amounts of arenes, TiCl3, and Li/Mg in THF or DME. Among the LVT reagents screened, TiCl3 - Li-naphthalene - THF (reagent I) was the best for coupling of carbonyls to olefins. The reagent could carry out the McMurry olefination of both aromatic and aliphatic substrates at a lower temperature and in a much reduced time as compared to the conventional procedures. Subtle changes in the method of preparation of the LVT reagents influenced the stereoisomeric ratio of the olefins. The reagent was also useful for the synthesis of O- and N- heterocycles and vicinal diamines via intramolecular carbonyl coupling and reductive duplication of imines, respectively.

Activation of Low-Valent Titanium Reagents with Iodine: Facile Low-Temperature McMurry Reaction and N/O-Debenzylation/Deallylation

A highly reactive, low-valent titanium (LVT) reagent has been prepared by the addition of substoichiometric amounts of iodine to the LVT species generated by Rieke's method (TiCl3-Li-THF). While the conventional McMurry reaction requires high temperatures and prolonged reaction times for the generation of olefins, the present activated LVT reagent is able to effect the reductive coupling of aliphatic as well as aromatic carbonyls to the corresponding olefins at lower temperatures and much reduced reaction times. The protocol is also useful for the intramolecular coupling reactions leading to the one-step synthesis of heterocycles. The temperature-controlled McMurry reaction provides enhanced diastereoselectivity and features an excellent chemoselectivity. In addition to the McMurry reaction, other SET-induced carbon-heteroatom (O, N) bond cleavages can also be carried out with the activated reagent at a fast rate and at a low temperature in high yields.

Synthesis of O-Heterocycles via Intramolecular Reductive Deoxygenation of o-Aroyloxyacetophenones: One-step Synthesis of Benzofurans

A one-step synthesis of benzofurans via intramolecular reductive coupling of o-aroyloxyacetophenones using titanium(IV) chloride and zinc is described.