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1.
JACS Au ; 1(9): 1506-1513, 2021 Sep 27.
Artigo em Inglês | MEDLINE | ID: mdl-34604859

RESUMO

Under the shielding effect of nanomicelles, a sustainable micellar technology for the design and convenient synthesis of ligand-free oxidizable ultrasmall Pd(0) nanoparticles (NPs) and their subsequent catalytic exploration for couplings of water-sensitive acid chlorides in water is reported. A proline-derived amphiphile, PS-750-M, plays a crucial role in stabilizing these NPs, preventing their aggregation and oxidation state changes. These NPs were characterized using 13C nuclear magnetic resonance (NMR), infrared (IR), and surface-enhanced Raman scattering (SERS) spectroscopy to evaluate the carbonyl interactions of PS-750-M with Pd. High-resolution transmission electron microscopy (HRTEM) and energy-dispersive X-ray spectroscopy (EDX) studies were performed to reveal the morphology, particle size distribution, and chemical composition, whereas X-ray photoelectron spectroscopy (XPS) measurements unveiled the oxidation state of the metal. In the cross-couplings of water-sensitive acid chlorides with boronic acids, the micelle's shielding effect and boronic acids plays a vital role in preventing unwanted side reactions, including the hydrolysis of acid chlorides under basic pH. This approach is scalable and the applications are showcased in multigram scale reactions.

2.
J Org Chem ; 81(8): 3447-56, 2016 Apr 15.
Artigo em Inglês | MEDLINE | ID: mdl-26991511

RESUMO

A practical and highly effective one-pot synthesis of versatile heteroaryl ketones directly from carboxylic acids and heteroaryl halides under mild conditions is reported. This method does not require derivatization of carboxylic acids (preparation of acid chlorides, Weinreb amides, etc.) or the use of any additives/catalysts. A wide substrate scope of carboxylic acids with high functional group tolerance has also been demonstrated. The results reveal that the presence of an α-nitrogen on the halide substrate greatly improves the desired ketone formation.

3.
Org Lett ; 14(10): 2626-9, 2012 May 18.
Artigo em Inglês | MEDLINE | ID: mdl-22571722

RESUMO

A convenient and efficient procedure is described for the sulfamoylation of alcohols using N-(tert-butoxycarbonyl)-N-[(triethylenediammonium)sulfonyl]azanide (1). The ambient temperature stable reagent 1 reacts with phenols as well as primary and secondary alcohols to give high to modest yields. The relative reaction rate of substrates was determined (primary > phenol > secondary ≫ tertiary). The reagent's utility as a selective sulfamoylation reagent with polyols is also demonstrated.


Assuntos
Álcoois/química , Sulfonas/química , Aminas , Indicadores e Reagentes , Estrutura Molecular , Fenóis
4.
J Org Chem ; 61(8): 2713-2718, 1996 Apr 19.
Artigo em Inglês | MEDLINE | ID: mdl-11667103

RESUMO

A practical titanium-catalyzed synthesis of bicyclic cyclopentenones and allylic amines is described. The process converts enyne substrates to iminocyclopentenes using 10 mol % of the air- and moisture-stable precatalyst Cp(2)TiCl(2) in the presence of n-BuLi and triethylsilyl cyanide. The resulting iminocyclopentenes can be hydrolyzed to cyclopentenones in good yields or reduced to allylic silylamines with Red-Al or DIBALH. Treatment of the crude silylamines with acetyl chloride allows isolation of allylic amides in excellent yields.

5.
Convuls Ther ; 3(1): 54-59, 1987.
Artigo em Inglês | MEDLINE | ID: mdl-11940891

RESUMO

Present administration of electroconvulsive therapy (ECT) is safe for most patients. Succinylcholine is used and tolerated as one of several pharmacologic agents in the routine protocol. Relatively rare medical conditions, including pseudocholinesterase deficiency, cholinesterase inhibition, and severe neuromuscular disease, may complicate the use of succinylcholine. This article presents three cases in which the standard protocol was altered, using atracurium in place of succinylcholine to provide brief and well-controlled muscle relaxation. Atracurium is an alternative medication for ECT in those cases in which succinylcholine use is problematic.

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