924658-35-5Relevant articles and documents
Methylsulfenylation of Electrophilic Carbon Atoms: Reaction Development, Scope, and Mechanism
Pereira, Adriane A.,Pereira, Amanda S.,de Mello, Amanda C.,Carpanez, Arthur G.,Horta, Bruno A. C.,Amarante, Giovanni W.
, p. 1578 - 1582 (2017)
An innovative method for the methylsulfenylation of electrophilic carbons was explored. Cheap and commercially available dimethyl sulfoxide (DMSO) was used as a source of the –SCH3 group. Chalcone, dibenzylideneacetone, and Morita–Baylis–Hillma
On the development of a nucleophilic methylthiolation methodology
Carvalho, Bernardo Basbaum Portinho De Puga,Amaral, Adriane Antonia Pereira,De Castro, Pedro P?ssa,Ferreira, Fernanda Cerqueira Moreira,Horta, Bruno Araújo Cautiero,Amarante, Giovanni Wilson
, p. 5420 - 5426 (2020/08/03)
Methylthiolation reactions are usually explored to access organosulfur compounds using methanethiol, an extremely flammable and toxic compound. Herein, methylthiomethyl esters were successfully applied as novel methylthiolation reagents in a low cost, transition-metal-free methodology. These reagents allowed the methylthiolation of a wide scope of chalcones, acyl ester derivatives and Morita-Baylis-Hillman acetates with good group tolerance, affording the methylthiolated products in moderate to excellent yields. The reaction mechanism was investigated through several control experiments, as well as by theoretical calculations employing Density Functional Theory. The results strongly support that a sulfurane and a sulfonium ylide appear as key intermediates and that a Pummerer type rearrangement is also crucial for the formation of this novel reagent. Furthermore, the methylthiolation mechanism is likely to proceed through the nucleophilic attack of the reagent, followed by an entropically favoured step involving the acetate attack to the positively charged species, then releasing the product. This journal is
Fe(III)-Catalyzed Hydroallylation of Unactivated Alkenes with Morita-Baylis-Hillman Adducts
Qi, Jifeng,Zheng, Jing,Cui, Sunliang
, p. 1355 - 1358 (2018/03/09)
An Fe(III)-catalyzed hydroallylation of unactivated alkenes with Morita-Baylis-Hillman adducts via an Fe-catalyzed process is described. A variety of alkenes, including mono-, di-, and trisubstituted alkenes, could all smoothly convert to structural diver