143505-42-4Relevant articles and documents
Nondirected Copper-Catalyzed Sulfoxidations of Benzylic C-H Bonds
Yu, Hao,Li, Zhen,Bolm, Carsten
, p. 2076 - 2079 (2018/04/16)
A copper-catalyzed sulfoxidation of benzylic C-H bonds by nondirected oxidative C(sp3)-H activation was developed. The process proceeds via sulfenate anions, which are generated by base-triggered elimination of β-sulfinyl esters and benzyl radicals. The functional group tolerance is high, and the product yields are good.
3-bisalkylated-2-indolone derivative and preparation method thereof
-
, (2019/02/26)
The invention provides a 3-bisalkylated-2-3-bisalkylated-2-indolone derivative. The derivative has a structural formula represented by a formula I shown in the description, wherein R1 and R2 are halogen or H. The invention further provides a preparation m
2-(trimethylsilyl)ethyl sulfoxides as a convenient source of sulfenate anions
Foucoin, Florian,Caupene, Caroline,Lohier, Jean-Francois,Santos, Jana Sopkova De Oliveira,Perrio, Stephane,Metzner, Patrick
, p. 1315 - 1324 (2008/02/13)
The present report describes the novel and smooth generation of sulfenate salts by fluoride-mediated cleavage of 2-(trimethylsilyl)ethyl sulfoxides. Efficiency of the process was elucidated through further reaction with alkyl halides to give stable sulfox
Oxidative fragmentations of 2-(trimethylsilyl)ethyl sulfoxides - Routes to alkane-, arene-, and highly substituted 1-alkenesulfinyl chlorides
Schwan, Adrian L.,Strickler, Rick R.,Dunn-Dufault, Robert,Brillon, Denis
, p. 1643 - 1654 (2007/10/03)
The preparation of a collection of alkyl, aryl, and 1-alkenyl 2-(trimethylsilyl)ethyl sulfoxides is outlined, using mostly vinyltrimethylsilane or 2-(trimethylsilyl)ethanesulfenyl chloride (5) as key starting materials. The 2-(trimethylsilyl)ethyl group can be cleaved from many of the sulfoxides under oxidative fragmentation conditions using sulfuryl chloride and the reaction represents a new protocol for sulfinyl chloride synthesis. The method is suitable for most alkane- and arenesulfinyl chlorides (3), but is limited to highly substituted vinylic sulfinyl chlorides. 1-Alkenyl 2-(trimethylsilyl)ethyl sulfoxides with reduced double bond substitution (6, 7, 11) succumb to reactions involving chlorination of the double bond. The β-effect of silicon is invoked to explain the ability of the 2-(trimethylsilyl)ethyl group to induce C-S bond scission under the oxidative cleavage reaction conditions. A mechanism is offered to account for the role played by the β-silicon atom of the 2-(trimethylsilyl)ethyl group. Indeed, the silicon atom is self-sacrificial in that it diverts the course of the reaction from the usual α-carbon chlorination mode to one of oxidative cleavage, whereby the 2-(trimethylsilyl)ethyl group is lost. The overall reaction calls upon the ability of silicon atoms to donate electron density by hyperconjugation.
The reaction of 2-trimethylsilylethyl sulfoxides with sulfuryl chloride. A fragmentation route to sulfinyl chlorides
Schwan,Dufault
, p. 3973 - 3974 (2007/10/02)
Sulfinyl chlorides were prepared in good to excellent yields by reacting aryl or alkyl 2-trimethylsilylethyl sulfoxides with SO2Cl2.