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1.
Org Lett ; 22(3): 950-955, 2020 Feb 07.
Artigo em Inglês | MEDLINE | ID: mdl-31961696

RESUMO

Deaminative functionalization of aliphatic primary amines has great synthetic utility. Herein, we describe a Ni-catalyzed reductive deaminative cross-electrophile coupling reaction between Katritzky salts and aromatic amides. This work provides examples of the synthesis of various ketones from alkylpyridinium salts, including both primary and secondary alkylamines. Given its mild reaction conditions and high functional group tolerance, this cross-coupling strategy is expected to be useful for late-stage functionalization of complex compounds.

2.
J Org Chem ; 84(4): 2339-2345, 2019 Feb 15.
Artigo em Inglês | MEDLINE | ID: mdl-30656930

RESUMO

Acetetracenylene-1,2-dione reacted with 3-ethylrhodanine in the presence of piperidine and Hantzsch ester via a Knoevenagel condensation-reduction sequence to give a tetracene-rhodanine adduct. This reduced Knoevenagel product exhibited magenta luminescence with a fluorescence quantum yield of φ = 0.34 and fluorescence lifetime of τ = 13.2 ns in toluene. Electrochemical studies and charge carrier transport measurements revealed ambipolar properties with hole and electron mobilities of 5.1 × 10-7 and 1.6 × 10-4 cm2/(V s), respectively.

3.
Org Lett ; 20(3): 570-573, 2018 02 02.
Artigo em Inglês | MEDLINE | ID: mdl-29350039

RESUMO

An example of Rh-catalyzed C-H activation with methyl trifluoroacrylate for the synthesis of fluoroolefins and heterocycles (benzoindolizines) is reported. The types of products were determined by the directing group. The benzoindolizines and fluoroolefins were obtained by using pyridine and pyrazole as the directing group, correspondingly. These transformations present a number of advantages, such as oxidant-free reaction conditions and broad functional group tolerance. Moreover, this reaction greatly extends the application of fluoroolefins.

4.
Angew Chem Int Ed Engl ; 54(44): 12957-61, 2015 Oct 26.
Artigo em Inglês | MEDLINE | ID: mdl-26338141

RESUMO

A novel copper-catalyzed regiodivergent alkylboration of alkenes with bis(pinacolato)diboron and alkyl halides has been developed. The regioselectivity of the alkylboration was controlled by subtle differences in the ligand structure. The reaction thus enables the practical, regiodivergent synthesis of two different alkyl boronic esters with complex structures from a single alkene.


Assuntos
Alcenos/química , Compostos de Boro/síntese química , Cobre/química , Compostos Organometálicos/química , Compostos de Boro/química , Catálise , Ligantes , Estrutura Molecular , Estereoisomerismo
5.
Angew Chem Int Ed Engl ; 54(28): 8231-5, 2015 Jul 06.
Artigo em Inglês | MEDLINE | ID: mdl-26032302

RESUMO

An unprecedented Pd-catalyzed regioselective activation of gem-difluorinated cyclopropanes induced by C-C bond cleavage is reported. It provides a general and efficient access to a variety of 2-fluoroallylic amines, ethers, esters, and alkylation products in high Z-selectivity, which are important skeletons in many biologically active molecules. In addition, the transformation represents the first general application of gem-difluorinated cyclopropanes as reaction partners in transition-metal-catalyzed cross-coupling reaction.


Assuntos
Alquilação/fisiologia , Ciclopropanos/química , Halogenação/fisiologia , Paládio/química , Catálise , Estrutura Molecular , Estereoisomerismo
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