37780-82-8Relevant articles and documents
Ruthenium-catalyzed decarboxylative C-S cross-coupling of carbonothioate: synthesis of allyl(aryl)sulfide
Zheng, Ren-Hua,Guo, Hai-Chang,Chen, Ting-Ting,Huang, Qing,Huang, Guo-Bo,Jiang, Hua-Jiang
, p. 25123 - 25126 (2018/07/29)
A novel ruthenium-catalyzed decarboxylative cross-coupling of carbonothioate is disclosed. This method provides straightforward access to the corresponding allyl(aryl)sulfide derivatives in generally good to excellent yields under mild conditions and feat
Rh(II)-Catalyzed [2,3]-Sigmatropic Rearrangement of Sulfur Ylides Derived from Cyclopropenes and Sulfides
Zhang, Hang,Wang, Bo,Yi, Heng,Zhang, Yan,Wang, Jianbo
supporting information, p. 3322 - 3325 (2015/07/15)
(Chemical Equation Presented) A new type of Rh2(OAc)4-catalyzed [2,3]-sigmatropic rearrangement of sulfur ylides is reported. A series of cyclopropenes were successfully employed for [2,3]-sigmatropic rearrangement by a reaction with either allylic or propargylic sulfides. Under the optimized conditions, the reaction afforded the products in moderate to excellent yields. In these transformations, the vinyl metal carbenes generated in situ from the cyclopropenes were effectively trapped by sulfides, resulting in the formation of corresponding products upon [2,3]-sigmatropic rearrangements.
Fast ruthenium-catalysed allylation of thiols by using allyl alcohols as substrates
Zaitsev, Alexey B.,Caldwell, Helen F.,Pregosin, Paul S.,Veiros, Luis F.
experimental part, p. 6468 - 6477 (2010/02/28)
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*)(n3CH5)(CH 3CN)2](PF6)2 (2; Cp* = pentamethylcyclopentadienyl) or a combination of [Ru(Cp*)(CH 3CN)3](PF6) and camphor sulfonic acid. Quantitative conversion is normal and the catalyst possesses high functional-group tolerance. The use of [Ru(Cp*)(CH3CN) 3](PF6) 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/1) 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 6-complexes are not relevant for the catalytic system. Moreover, the DFT results indicate that l)any rf-complexes from the acids RC6H4SO 3H 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, RC6H4SO3and 3) a sulfonate O-atom complex will be difficult to detect.