Ru complexes bearing bidentate carbenes: from innocent curiosity to uniquely effective catalysts for olefin metathesis

Hoveyda, Amir H.; Gillingham, Dennis; Veldhuizen, Joshua J. Van; Kataoka, Osamu; Garber, Steven B.; Kingsbury, Jason S.; Harrity, Joseph P. A.

doi:10.1039/b311496c

Cited by 339 publications

(187 citation statements)

References 78 publications

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“…We first investigated RCM of the α,β-unsaturated ester (85), derived from 84 by acylation with acryloyl chloride, using 1 mol% loading of the nitroderivative of the Hoveyda catalyst. [63][64][65][66] However, the desired product could not be isolated under a range of reaction conditions, presumably due to the presence of a less reactive conjugated ester function. We, therefore, turned our attention to employing a more reactive allyl ether as the precursor for RCM.…”

Section: Synthesis Of (−)-Securininementioning

confidence: 99%

Investigation of Innovative Synthesis of Biologically Active Compounds on the Basis of Newly Developed Reactions

Honda

2012

Chem. Pharm. Bull.

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Synthesis of biologically active compounds, including natural products and pharmaceutical agents, is an important and interesting research area since the large structural diversity and complexity of bioactive compounds make them an important source of leads and scaffolds in drug discovery and development. Many structurally and also biologically interesting compounds, including marine natural products, have been isolated from nature and have also been prepared on the basis of a computational design for the purpose of developing medicinal chemistry. In order to obtain a wide variety of derivatives of biologically active compounds from the viewpoint of medicinal chemistry, it is essential to establish efficient synthetic procedures for desired targets. Newly developed reactions should also be used for efficient synthesis of desired compounds. Thus, recent progress in the synthesis of biologically active compounds by focusing on the development of new reactions is summarized in this review article.

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Section: Synthesis Of (−)-Securininementioning

confidence: 99%

Investigation of Innovative Synthesis of Biologically Active Compounds on the Basis of Newly Developed Reactions

Honda

2012

Chem. Pharm. Bull.

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“…Our purpose in this section is to trace some of the major current themes in design of new ruthenium catalysts, rather than to undertake a comprehensive review. Overviews of recent developments in the design of individual catalyst classes have appeared elsewhere [32][33][34][35][36][108][109][110].…”

Section: Advances In Catalyst Designmentioning

confidence: 99%

“…Aryloxide complexes C50 and C51 are a recent addition to the family of highly active metathesis catalysts; C52, in comparison, exhibits modest activity, but opens the door to Ru-catalyzed asymmetric metathesis, as discussed below [108,139,149]. The activity of C50 and C51 is due in part to the low steric constraints within these complexes: steric demand is minimized by the planarity of the aryloxide and pyridine donors, in conjunction with an essentially twodimensional IMes ligand [150].…”

Section: Pseudohalide Catalystsmentioning

confidence: 99%

Ruthenium‐Catalyzed Ring‐Closing Metathesis: Recent Advances, Limitations and Opportunities

Conrad

Fogg

2006

ChemInform

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Recent advances in ruthenium-catalyzed ring closing metathesis are discussed, in context of both substrate and catalyst parameters. As well as thermodynamic (substrate) constraints on ring-closing, root causes and effects of non-ideal catalytic performance are examined. Key substrate parameters are outlined, with a particular focus on the balance between oligomerization and ring-closing in RCM macrocyclization reactions. Advances in catalyst design are examined from a mechanistic viewpoint, including initiation requirements, catalyst deactivation, and opportunities resulting from incorporation of pseudohalide ligands. An overview of methods for reducing ruthenium residues in organic products to ppm levels is presented.

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“…Estas transformações obviamente devem ser realizadas sob alta diluição para evitar a formação de material polimérico e, assim, promover a reação intramolecular. Hoveyda e colaboradores 23 empregaram esta estratégia na síntese de cromenos 44 (Esquema 37), estruturas encontradas em produtos naturais, largamente empregados na indústria farmacêutica e com relevantes atividades biológicas. A seqüência RCM/ROM foi proposta pelos autores, porém também pode se imaginar chegar aos produtos 44 pela sequência ROM/RCM.…”

Section: Processo Rom/rcmunclassified

A reação de metátese de olefinas: reorganização e ciclização de compostos orgânicos

Frederico¹,

Brocksom²,

Brocksom³

2005

Quím. Nova

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Recebido em 12/7/04; aceito em 13/10/04; publicado na web em 4/2/05 THE OLEFIN METATHESIS REACTION: REORGANIZATION AND CICLIZATION OF ORGANIC COMPOUNDS. The olefin metathesis reaction allows the exchange of complex alkyl units between two olefins, with the formation of a new olefinic link and a sub-product olefin usually ethylene. This reaction has found extensive application in the last ten years with the development of the Grubbs and Schrock catalysts, in total synthesis of complex organic molecules, as opposed to the very important use in the petrochemical industry with relatively simple molecules. This review intends to trace a historical and mechanistic pathway from industry to academy, before illustrating the more recent advances.Keywords: olefin metathesis; ring-closing metathesis; cross metathesis. No sentido químico, a palavra metátese descreve, por tradução direta do grego "troca de posição", a troca de ligações covalentes entre dois alcenos (ou olefinas) ou entre um alceno e um alcino. Na química de olefinas, ela se refere a uma redistribuição do esqueleto carbônico (Esquema 1), no qual ligações duplas carbono-carbono são rearranjadas na presença de um complexo metal-carbeno, representando um método catalítico de quebra e de formação de ligações múltiplas carbono-carbono. Esta reação é conhecida na petroquímica e na química dos polímeros há mais de 40 anos 1 , mas só na década de noventa, com o advento de novos e eficientes catalisadores, desenvolvidos principalmente pelos grupos de pesquisa de Schrock 2,3 e Grubbs 4,5 , ela emergiu como uma potente ferramenta na química orgânica acadêmica. INTRODUÇÃOEstes novos catalisadores proporcionaram um grande aumento no número de aplicações desta reação, atraindo a atenção de quí-micos acadêmicos e industriais. Atualmente, estas aplicações estão relacionadas com a metátese entre dois alcenos (metátese de dienos) ou entre um alceno e um alcino (metátese de eninos) mostradas no Esquema 2.A reação entre duas olefinas distintas recebe o nome de metátese cruzada (CM do inglês "cross-metathesis") e a sua versão intramolecular, a reação entre duas ligações duplas na mesma molécula, é conhecida como metátese de fechamento de anel (RCM; "ring-closing metathesis"). A formação de dienos não conjugados a partir de olefinas cíclicas é conhecida por abertura de anel por metátese (ROM; "ring-opening metathesis") e, formalmente é a reação inversa da RCM. Reações de polimerização podem ocorrer entre dienos acíclicos (ADMET; "acyclic diene metathesis polymerization") ou ainda com alcenos cíclicos, através do processo de abertura de anel por metátese (ROMP; "ring-opening metathesis polymerization"). As combinações dos processos de CM, RCM e ROM deram origem a uma nova e eficiente estratégia para

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Ru complexes bearing bidentate carbenes: from innocent curiosity to uniquely effective catalysts for olefin metathesis

Cited by 339 publications

References 78 publications

Investigation of Innovative Synthesis of Biologically Active Compounds on the Basis of Newly Developed Reactions

Investigation of Innovative Synthesis of Biologically Active Compounds on the Basis of Newly Developed Reactions

Ruthenium‐Catalyzed Ring‐Closing Metathesis: Recent Advances, Limitations and Opportunities

A reação de metátese de olefinas: reorganização e ciclização de compostos orgânicos

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