82946-84-7Relevant articles and documents
Palladium-catalyzed three-component cascade arylthiolation with aryldiazonium salts asS-arylation sources
Li, Jianxiao,Tang, Hao,Lin, Zidong,Yang, Shaorong,Wu, Wanqing,Jiang, Huanfeng
, p. 4071 - 4078 (2020/06/09)
A novel and efficient palladium-catalyzed three-component cascade cyclization/arylthiolation has been developed for the assembly of diverse 3-sulfenylindole and 3-sulfenylbenzofuran derivatives from 2-alkynylamines and 2-alkynylphenols, aryldiazonium salts, and Na2S2O3under aerobic conditions with PEG-200 as an environmentally benign medium. The current study features exceptional functional group tolerance without additional ligands, oxidants or silver salts, and eco-friendly mild reaction conditions. The ionic liquid [C2OHmim]Cl plays a crucial role in this protocol as an environmentally friendly additive. Notably, this procedure represents the first example of the use of aryldiazonium salts as directS-arylation sources in this type of chemical transformation.
Direct, Metal-free C(sp2)?H Chalcogenation of Indoles and Imidazopyridines with Dichalcogenides Catalysed by KIO3
Rafique, Jamal,Saba, Sumbal,Franco, Marcelo S.,Bettanin, Luana,Schneider, Alex R.,Silva, Lais T.,Braga, Antonio L.
supporting information, p. 4173 - 4180 (2018/02/06)
Herein, we report a greener protocol for the synthesis of 3-Se/S-indoles and imidazo[1,2-a]pyridines through direct C(sp2)?H bond chalcogenation of heteroarenes with half molar equivalents of different dichalcogenides, using KIO3 as a non-toxic, easy-to-handle catalyst and a stoichiometric amount of glycerol. The reaction features are high yields, based on atom economy, easy performance on gram-scale, metal- and solvent-free conditions as well as applicability to different types of N-heteroarenes.
NH4I-catalyzed chalcogen(S/Se)-functionalization of 5-membered N-heteroaryls under metal-free conditions
Bettanin, Luana,Saba, Sumbal,Doerner, Carlos V.,Franco, Marcelo S.,Godoi, Marcelo,Rafique, Jamal,Braga, Antonio L.
, p. 3971 - 3980 (2018/06/12)
Herein, we described the NH4I-catalyzed C–H bond chalcogenation of N-heteroaryls in the presence of a minimum amount of DMSO/H2O/acetic acid as additives (2.5/2.5/1 M equiv., respectively), under metal-free conditions. Under optimized conditions, a wide variety of sulfenyl/selenyl imidazo[1,2-α]pyridines were prepared in very good yields. Moreover, the present approach was also highly efficient for the chalcogenation of different 5-membered N-heteroaryls, e.g., indole, imidazothiazole, indazole and imidazopyrimidine derivatives.