24309-31-7Relevant articles and documents
Yb(iii)-catalysedsyn-thioallylation of ynamides
Dutta, Shubham,Gandon, Vincent,Gogoi, Manash Protim,Mallick, Rajendra K.,Prabagar, B.,Sahoo, Akhila K.,Vanjari, Rajeshwer,Yang, Shengwen
supporting information, p. 7521 - 7524 (2021/08/05)
Reported herein is asyn-thioallylation of ynamides incorporating a sulfide moiety at the α-position and an allyl group at the β-position of the ynamide. The transformation is successful under ytterbium(iii)-catalysis, providing access to highly substituted thioamino-skipped-dienes with broad substrate scope. Thus, tetrasubstituted olefins (with four different functional groups: amide, phenyl, thioaryl/alkyl, and allyl on the carbon centers) are made in a single step from readily accessible ynamides, preserving complete atom economy. The reaction can be extended to the synthesis of selenoamino dienes by ynamidesyn-selenoallylation. DFT studies and control experiments provide insight into the reaction mechanism.
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.
Catalyst-free imidation of allyl sulfides with chloramine-T and subsequent [2,3]-sigmatropic rearrangement
Jiang, Yubo,Mo, Fanyang,Qiu, Di,Kuang, Chunxiang,Zhang, Yan,Wang, Jianbo
, p. 2029 - 2035 (2012/11/07)
A facile synthesis of various allyl sulfonamides based on imidation of allyl sulfides with chloramine-T and subsequent [2,3]-sigmatropic rearrangement has been achieved without metal catalysts. The reaction completes smoothly within 10 min, providing excellent yields in environment friendly solvent of alcohol. Functional groups such as bromine, hydroxyl, protected amido and aldehyde are tolerant under this condition.
Selective allylation of arenethiols using water-soluble palladium complex catalyst in recyclable water/hexane biphasic media
Komine, Nobuyuki,Sako, Akari,Hirahara, Shin-Ya,Hirano, Masafumi,Komiya, Sanshiro
, p. 246 - 247 (2007/10/03)
Allylation of arenethiols by allylic alcohol with sterically hindered carbon of the allylic moiety is smoothly catalyzed by Pd(OAc)2/TPPTS in biphasic water/hexane media under ambient conditions. The catalyst water layer can be repeatedly reuse
Ytterbium metal promoted allylation of disulfides with allyl bromide
Su, Weike,Li, Yongshu,Zhang, Yongmin
, p. 2101 - 2106 (2007/10/03)
In the presence of a catalytic amount of methyliodide, ytterbium metal can promote the reductive cleavage of the S-S bond in disufides 1 to give ytterbium thiolates 2 which then react with allyl bromide to form the corresponding allylic sulfides 3 in good yields under mild and neutral conditions.
Asymmetric Copper-Catalyzed [2,3]-Sigmatropic Rearrangements of Alkyl- and Aryl-Substituted Allyl Sulfides
McMillen, Douglas W.,Varga, Norbert,Reed, Beth Ann,King, Claudia
, p. 2532 - 2536 (2007/10/03)
The asymmetric copper-catalyzed generation and subsequent [2,3]-sigmatropic rearrangement of sulfur ylides is strongly dependent on the structure of the starting allyl sulfide. A series of alkyl and aryl substituted allyl Sulfides (2a-i) were reacted with
