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1.
Org Lett ; 2020 Feb 11.
Artigo em Inglês | MEDLINE | ID: mdl-32043889

RESUMO

An unprecedented copper-catalyzed reaction of sulfoxonium ylides and anthranils is reported that enables an easy access to 2,3-diaroylquinolines through a [4+1+1] annulation. Copper-catalyzed homocoupling of sulfoxonium ylides provided α,α,ß-tricarbonyl sulfoxonium ylides, which provides a strategy to extend the carbon chain through C-C bond formation. The utility of the products as well as the mechanistic details of the process are presented.

2.
J Org Chem ; 84(19): 12301-12313, 2019 Oct 04.
Artigo em Inglês | MEDLINE | ID: mdl-31482711

RESUMO

A copper-catalyzed protocol for the construction of various 2-aryl(alkyl)-3-acylquinolines or 3-arylquinolines using readily available anthranils and 1,3-diketones or aldehydes as starting materials is reported herein. Dioxygen as the sole oxidant and hexafluoroisopropanol as the solvent play an important role in both procedures. This ring-opening/reconstruction strategy involving N-O bond cleavage and C-N/C-C bond formation features high yields and broad substrate scope.

3.
Org Biomol Chem ; 17(24): 5902-5907, 2019 06 18.
Artigo em Inglês | MEDLINE | ID: mdl-31140526

RESUMO

Copper-catalyzed coupling of α-keto acids with anthranils is reported for the synthesis of α-ketoamides. This process involves N-O/C-O bond cleavages and C-N bond formation. Furthermore, the decarboxylation of α-keto acids can be successfully suppressed under redox-neutral conditions.

4.
J Org Chem ; 82(23): 12892-12898, 2017 12 01.
Artigo em Inglês | MEDLINE | ID: mdl-29110477

RESUMO

A transition-metal-free protocol for the construction of C-S bonds has been developed. Acetylacetone acts as a new and green aryl source for the synthesis of polysubstituted diarylsulfides bearing a free hydroxy group and a ketone group, which provides a new access to a series of flavonoids containing a thioaryl group. In addition, a series of α-thioarylcarbonyl compounds are obtained in good to excellent yields.

5.
Chemistry ; 21(3): 1004-8, 2015 Jan 12.
Artigo em Inglês | MEDLINE | ID: mdl-25470781

RESUMO

An efficient, highly stereoselective asymmetric synthesis of fully functionalized cyclopentanes bearing an oxindole moiety and several other functional groups in one pot has been developed. Key step is an organocatalytic triple Michael domino reaction forming three C-C bonds and six stereocenters, including a quaternary one. Starting from equimolar amounts of simple substrates, a high molecular complexity can be reached after a Wittig olefination in one pot. The new protocol can easily be scaled up to gram amounts.


Assuntos
Ciclopentanos/química , Indóis/química , Catálise , Cristalografia por Raios X , Ciclização , Conformação Molecular , Oxindois , Estereoisomerismo
6.
Chemistry ; 19(25): 8144-52, 2013 Jun 17.
Artigo em Inglês | MEDLINE | ID: mdl-23616246

RESUMO

An efficient catalytic system for Sonogashira-Hagihara-type reactions displaying ligand acceleration in the copper-catalyzed formation of C(sp²)-C(sp) bonds is described. The structure of the ligand plays a key role for the coupling efficiency. Various copper sources show excellent catalytic activity, even in sub-mol% quantities. A wide variety of substituents is tolerated in the substrates. Mechanistic details have been revealed by kinetic measurements and DFT calculations.

7.
Chemistry ; 19(10): 3302-5, 2013 Mar 04.
Artigo em Inglês | MEDLINE | ID: mdl-23401050

RESUMO

CH(3)CN and O(2) do the trick! A copper-mediated direct oxidative cross-coupling of 2-(het)aryl-1,3,4-oxadiazoles with polyhaloarenes under mild reaction conditions has been developed (see scheme). The process provides a concise access to biaryl structures containing polyhaloarenes, which are of interest in the fields of pharmaceuticals and functional materials. Acetonitrile and oxygen play crucial roles.

8.
Chem Commun (Camb) ; 48(92): 11307-9, 2012 Nov 28.
Artigo em Inglês | MEDLINE | ID: mdl-23072812

RESUMO

A convenient transition metal-free procedure for the direct thiolation of 1,3,4-oxadiazole C-H bonds using diaryl disulfides has been developed. Other substrates including indole, benzothiazole, N-phenylbenzimidazole, and caffeine were also thiolated in this manner, providing the corresponding products in good to excellent yields.


Assuntos
Oxidiazóis/química , Elementos de Transição/química , Benzotiazóis/química , Cafeína/química , Carbono/química , Hidrogênio/química , Indóis/química , Compostos de Sulfidrila/química
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