66164-72-5Relevant academic research and scientific papers
Iron-Induced regio- and stereoselective addition of sulfenyl chlorides to alkynes by a radical pathway
Iwasaki, Masayuki,Fujii, Tomoya,Nakajima, Kiyohiko,Nishihara, Yasushi
, p. 13880 - 13884 (2015/01/16)
The radical addition of the ClS s-bond in sulfenyl chlorides to various C~C triple bonds has been achieved with excellent regio- and stereoselectivity in the presence of a catalytic amount of a common iron salt. The reaction is compatible with a variety of functional groups and can be scaled up to the gram-scale with no loss in yield. As well as terminal alkynes, internal alkynes underwent stereodefined chlorothiolation to provide tetrasubstituted alkynes. Preliminary mechanistic investigations revealed a plausible radical process involving a sulfur-centered radical intermediate via iron-mediated homolysis of the ClS bond. The resulting chlorothiolation adducts can be readily transformed to the structurally complex alkenyl sulfides by cross-coupling reactions. The present reaction can also be applied to the complementary synthesis of the potentially useful bis-sulfoxide ligands for transition-metal-catalyzed reactions.
A New Version of the Peterson Olefination Using Bis(trimethylsilyl)methyl Derivatives and Fluoride Ion as Catalyst
Palomo, Claudio,Aizpurua, Jesus M.,Garcia, Jesus M.,Ganboa, Inaki,Cossio, F. P.,et al.
, p. 2498 - 2503 (2007/10/02)
Reaction between a variety of bis(trimethylsilyl)methyl derivatives and carbonyl compounds under fluoride ion as catalyst is described.The reaction works especially well with nonenolizable carbonyl compounds to give the expected alkenes in high yields and, in some cases, with high stereoselectivity.Application of this methodology to an intramolecular alkenation providing a tricyclic benzocarbacephem ring system is also described.
REACTIONS OF PHENYLTHIOTRIMETHYISILYLMETHYLLITHIUM: PREPARATION OF α-PHENYLTHIOKETONES AND ADDITIONS TO 2-CYCLOHEXEN-1-ONE
Ager, David J.
, p. 2803 - 2806 (2007/10/02)
Phenylthiotrimethylsilylmethyllithium(1) was reacted with a variety of electrophiles, including some containing two functional groups. α-Phenylthioketones were obtained from the reaction with esters.The anion(1) underwent either 1,2- or 1,4-addition, depe
