Your browser doesn't support javascript.
loading
Mostrar: 20 | 50 | 100
Resultados 1 - 7 de 7
Filtrar
Mais filtros

Base de dados
Tipo de estudo
Tipo de documento
Intervalo de ano de publicação
1.
Org Biomol Chem ; 19(40): 8789-8793, 2021 Oct 20.
Artigo em Inglês | MEDLINE | ID: mdl-34585716

RESUMO

The development of electrocatalytic synthetic methods hinges on efficient molecular catalysts. Triarylamines are well-known redox catalysts because of the good stability of their corresponding amine radical cations. Herein we show that tris(4-(tert-butyl)phenyl)amine decomposes unexpectedly during electrolysis in MeOH/THF to afford a tetraarylhydrazine, 1,1,2,2-tetrakis(4-(tert-butyl)phenyl)hydrazine. In addition, we have applied this tetraarylhydrazine, which is either preprepared or formed in situ from tris(4-(tert-butyl)phenyl)amine, as an electrocatalyst for the synthesis of imidazopyridines and related N-heteroaromatic compounds through intramolecular [3 + 2] annulation. This metal-free electrocatalytic method provides straightforward access to the N-heteroaromatic compounds from readily available materials without the need for external chemical oxidants.

2.
Beilstein J Org Chem ; 15: 795-800, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-30992728

RESUMO

A diastereoselective approach to axially chiral imidazopyridine-containing biaryls has been developed. The reactions proceed through a radical cyclization cascade to construct the biaryls with good to excellent central-to-axial chirality transfer.

3.
Angew Chem Int Ed Engl ; 57(6): 1636-1639, 2018 02 05.
Artigo em Inglês | MEDLINE | ID: mdl-29266679

RESUMO

We have developed a unified strategy for preparing a variety of imidazo-fused N-heteroaromatic compounds through regiospecific electrochemical (3+2) annulation reaction of heteroarylamines with tethered internal alkynes. The electrosynthesis employs a novel tetraarylhydrazine as the catalyst, has a broad substrate scope, and obviates the need for transition-metal catalysts and oxidizing reagents.

4.
Angew Chem Int Ed Engl ; 55(6): 2226-9, 2016 Feb 05.
Artigo em Inglês | MEDLINE | ID: mdl-26732232

RESUMO

Oxidative generation of synthetically important amidyl radicals from N-H amides is an appealing and yet challenging task. Previous methods require a stoichiometric amount of a strong oxidant and/or a costly noble-metal catalyst. We report herein the first electrocatalytic method that employs ferrocene (Fc), a cheap organometallic reagent, as the redox catalyst to produce amidyl radicals from N-aryl amides. Based on this radical-generating method, an efficient intramolecular olefin hydroamidation reaction has been developed.

5.
Angew Chem Int Ed Engl ; 55(32): 9168-72, 2016 08 01.
Artigo em Inglês | MEDLINE | ID: mdl-27240116

RESUMO

Indoles and azaindoles are among the most important heterocycles because of their prevalence in nature and their broad utility in pharmaceutical industry. Reported herein is an unprecedented noble-metal- and oxidant-free electrochemical method for the coupling of (hetero)arylamines with tethered alkynes to synthesize highly functionalized indoles, as well as the more challenging azaindoles.

6.
Chem Commun (Camb) ; 51(22): 4576-8, 2015 Mar 18.
Artigo em Inglês | MEDLINE | ID: mdl-25607771

RESUMO

The first enantioselective total synthesis of (+)-methoxystemofoline (2) and (+)-isomethoxystemofoline (3) has been reported. The synthesis employed the halide-assisted bromotropanonation method that we developed recently to construct the core structure, and Overman's strategy for the implementation of the butenolide moiety. Through this work, the structure of methoxystemofoline was revised as with an E-alkene, and its absolute configuration was established.


Assuntos
Alcaloides/síntese química , Compostos Heterocíclicos de 4 ou mais Anéis/síntese química , Alcaloides/química , Cristalografia por Raios X , Compostos Heterocíclicos de 4 ou mais Anéis/química , Modelos Moleculares , Estrutura Molecular , Estereoisomerismo
SELEÇÃO DE REFERÊNCIAS
Detalhe da pesquisa