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1.
Chemistry ; 21(24): 8812-5, 2015 Jun 08.
Artigo em Inglês | MEDLINE | ID: mdl-25950870

RESUMO

The so-called magic methyl effect significantly boosts the bioactivities and physical properties of pharmacologically active drugs. Direct introduction of the methyl group by CH activation was accomplished with a versatile iron catalyst, which enabled the CH methylation of (hetero)benzamides, anilides, alkenes, and even alkanes by triazole assistance in a chemo-, site- and diastereo-selective fashion.


Assuntos
Amidas/química , Anilidas/química , Ferro/química , Catálise , Metilação , Estrutura Molecular
2.
Angew Chem Int Ed Engl ; 53(15): 3868-71, 2014 Apr 07.
Artigo em Inglês | MEDLINE | ID: mdl-24596034

RESUMO

Modular 1,2,3-triazoles enabled iron-catalyzed CH arylations with broad scope. The novel triazole-based bidentate auxiliary is easily accessible in a highly modular fashion and allowed for user-friendly iron-catalyzed C(sp(2) )H functionalizations of arenes and alkenes with excellent chemo- and diastereoselectivities. The versatile iron catalyst also proved applicable for challenging C(sp(3) )H functionalizations, and proceeds by an organometallic mode of action. The triazole-assisted CH activation strategy occurred under remarkably mild reaction conditions, and the auxiliary was easily removed in a traceless fashion. Intriguingly, the triazole group proved superior to previously used auxiliaries.


Assuntos
Ferro/química , Triazóis/química , Catálise
3.
Org Lett ; 14(24): 6318-21, 2012 Dec 21.
Artigo em Inglês | MEDLINE | ID: mdl-23234384

RESUMO

Cationic ruthenium(II) complexes allowed for highly efficient oxidative annulations of aryl- and alkyl-substituted alkynes by 5-aryl-1H-pyrazoles. The C-H/N-H bond functionalization strategy furthermore proved applicable to the high-yielding activation of heteroaryl as well as alkenyl C-H bonds.

4.
Org Lett ; 14(16): 4110-3, 2012 Aug 17.
Artigo em Inglês | MEDLINE | ID: mdl-22849302

RESUMO

Cationic ruthenium(II) complexes enabled catalytic twofold C-H bond functionalizations with weakly coordinating aromatic esters in a highly chemo-, site- and diastereo-selective as well as site selective fashion. The oxidative Fujiwara-Moritani-type alkenylation provided step-economical access to diversely substituted styrenes and proved viable in an aerobic manner. Mechanistic studies were indicative of a reversible acetate-assisted cycloruthenation step.


Assuntos
Alcinos/química , Compostos Organometálicos/química , Catálise , Ésteres , Estrutura Molecular , Oxirredução , Rutênio/química , Estereoisomerismo
5.
Org Lett ; 14(3): 930-3, 2012 Feb 03.
Artigo em Inglês | MEDLINE | ID: mdl-22273364

RESUMO

An inexpensive cationic ruthenium(II) catalyst enabled the expedient synthesis of isocoumarins through oxidative annulations of alkynes by benzoic acids. This C-H/O-H bond functionalization process also proved applicable to the preparation of α-pyrones and was shown to proceed by rate-limiting C-H bond ruthenation.


Assuntos
Isocumarinas/síntese química , Pironas/síntese química , Rutênio/química , Catálise , Estrutura Molecular , Oxirredução
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