Transition Metal‐Free, Free‐Radical Sulfenylation of the α‐C(<i>sp</i><sup>3</sup>)−H Bond in Arylacetamides and Its Application Toward 2‐Thiomethyl Benzoxazoles Synthesis
Shanghui Tian, Chaoli Wang, Jianhui Xia, Jie‐Ping Wan, Yunyun Liu
Abstract
Abstract This paper reports the transition metal‐free C( sp 3 )−H sulfenylation of arylacetamides by using thiophenols as the sulfenyl reagents. The reactions take place in the presence of only K 3 PO 4 . Control experiments indicate that the reactions proceed via a featured sulfur‐centred free radical intermediate. In addition, the synthesis of 2‐thiomethyl benzoxazoles has been realized via the p ‐toluenesulfonic acid ( p ‐TSA) promoted annulation of the sulfenylated products. magnified image
Topics & Concepts
ChemistryReagentSulfurAnnulationTransition metalMedicinal chemistryFree-radical reactionRadicalStereochemistryCombinatorial chemistryOrganic chemistryCatalysisSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsRadical Photochemical Reactions