Domino C?S/C?N Bond Formation Using Well-Defined Copper-Phosphine Complex Catalyst: Divergent Approach to 3-Sulfenylated Indoles
A protocol was developed for the synthesis of 3-thioindoles in good-to-excellent yields involving sulfenylation between 2-nitrocinnamaldehydes and various thiols using a well-defined copper(I)-phosphine complex catalyst. This unconventional divergent approach involves in situ generation of indoles via domino C?S/C?N bond formation initiated by sulfa-Michael addition followed by intramolecular N-heteroannulation. This protocol shows good chemoselectivity and broad substrate scope. To briefly demonstrate the value of this approach, 2-benzoyl-3-sulfenylated indoles were prepared from commercially available 2-nitrochalcones and thiols. (Figure presented.).
Tamargo, Ramuel John Inductivo,Kim, Sung Hong,Lee, Yong Rok
p. 4005 - 4015
(2019/07/18)
Iodine-promoted selective 3-selanylation and 3-sulfenylation of indoles with dichalcogenides under mild conditions
A simple method was developed for the synthesis of 3-chalcogen indoles via iodine-promoted direct 3-selanyl- and 3-sulfenylation of indoles with dichalcogenides. The reaction was carried out smoothly in EtOH under air at room temperature, selectively givi
Iron-catalyzed sulfenylation of indoles with disulfides promoted by a catalytic amount of iodine
Selective sulfenylation of indoles with disulfides using iron(III) fluoride combined with iodine has been developed for the synthesis of sulfenylindoles. In the presence of iron(III) fluoride and iodine, a variety of disulfides underwent the reaction with indoles selectively to afford the corresponding sulfenylindoles in good to excellent yields. Moreover, reactions of indoles with 1,2-diphenyldiselane were also conducted under the same conditions, which smoothly afforded 3-selenylindoles in good yields. Georg Thieme Verlag Stuttgart - New York.