Source:http://linkedlifedata.com/resource/pubmed/id/19466722
| Subject | Predicate | Object | Context |
|---|---|---|---|
| pubmed-article:19466722 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:19466722 | lifeskim:mentions | umls-concept:C0038734 | lld:lifeskim |
| pubmed-article:19466722 | lifeskim:mentions | umls-concept:C0051225 | lld:lifeskim |
| pubmed-article:19466722 | lifeskim:mentions | umls-concept:C1710236 | lld:lifeskim |
| pubmed-article:19466722 | lifeskim:mentions | umls-concept:C0456962 | lld:lifeskim |
| pubmed-article:19466722 | pubmed:issue | 26 | lld:pubmed |
| pubmed-article:19466722 | pubmed:dateCreated | 2009-6-29 | lld:pubmed |
| pubmed-article:19466722 | pubmed:abstractText | Green and fast: Allylation of aromatic and aliphatic thiols, by using allyl alcohols as substrates, requires only minutes at ambient temperature with a Ru catalyst (see scheme). Quantitative conversion is normal and the catalyst possesses high functional-group tolerance.The allylation of aromatic and aliphatic thiols, by using allyl alcohols as substrates, requires only minutes at ambient temperature with either a Ru(IV) catalyst, [Ru(Cp*)(eta(3)-C(3)H(5))(CH(3)CN)(2)](PF(6))(2) (2; Cp*=pentamethylcyclopentadienyl) or a combination of [Ru(Cp*)(CH(3)CN)(3)](PF(6)) and camphor sulfonic acid. Quantitative conversion is normal and the catalyst possesses high functional-group tolerance. The use of [Ru(Cp*)(CH(3)CN)(3)](PF(6)) alone affords poor results. A comparison is made to the results from catalytic runs based on the use of carbonates rather than alcohols, by using 2 as the catalyst, and it is shown that the products from the alcohols are formed faster, so there is no advantage in using a carbonate substrate. The observed branched-to-linear (b/l) ratios when using substituted alcohols decrease with time suggesting that the catalysts isomerise the products. A new methodology from which one can select the desired isomeric product is proposed. DFT calculations and NMR spectroscopic measurements, by using an arene sulfonic acid as co-catalyst, suggest that eta(6)-complexes are not relevant for the catalytic system. Moreover, the DFT results indicate that 1) any eta(6)-complexes from the acids RC(6)H(4)SO(3)H result from deprotonation of the acid, 2) complexation of the thiol, via the deprotonated sulfur atom, is preferred over complexation of the O atom of the sulfonate, RC(6)H(4)SO(3) (-) and 3) a sulfonate O-atom complex will be difficult to detect. | lld:pubmed |
| pubmed-article:19466722 | pubmed:language | eng | lld:pubmed |
| pubmed-article:19466722 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:19466722 | pubmed:status | PubMed-not-MEDLINE | lld:pubmed |
| pubmed-article:19466722 | pubmed:month | Jun | lld:pubmed |
| pubmed-article:19466722 | pubmed:issn | 1521-3765 | lld:pubmed |
| pubmed-article:19466722 | pubmed:author | pubmed-author:VeirosLuis... | lld:pubmed |
| pubmed-article:19466722 | pubmed:author | pubmed-author:PregosinPaul... | lld:pubmed |
| pubmed-article:19466722 | pubmed:author | pubmed-author:ZaitsevAlexey... | lld:pubmed |
| pubmed-article:19466722 | pubmed:author | pubmed-author:CaldwellHelen... | lld:pubmed |
| pubmed-article:19466722 | pubmed:issnType | Electronic | lld:pubmed |
| pubmed-article:19466722 | pubmed:day | 22 | lld:pubmed |
| pubmed-article:19466722 | pubmed:volume | 15 | lld:pubmed |
| pubmed-article:19466722 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:19466722 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:19466722 | pubmed:pagination | 6468-77 | lld:pubmed |
| pubmed-article:19466722 | pubmed:dateRevised | 2009-8-4 | lld:pubmed |
| pubmed-article:19466722 | pubmed:year | 2009 | lld:pubmed |
| pubmed-article:19466722 | pubmed:articleTitle | Fast ruthenium-catalysed allylation of thiols by using allyl alcohols as substrates. | lld:pubmed |
| pubmed-article:19466722 | pubmed:affiliation | Laboratory of Inorganic Chemistry, ETHZ, Hönggerberg, 8093 Zürich, Switzerland. | lld:pubmed |
| pubmed-article:19466722 | pubmed:publicationType | Journal Article | lld:pubmed |