61899-66-9Relevant 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.
