84224-96-4Relevant academic research and scientific papers
Synthesis of Benzo[b]thiophenes through Rhodium-Catalyzed Three-Component Reaction using Elemental Sulfur
Moon, Sanghun,Kato, Moena,Nishii, Yuji,Miura, Masahiro
supporting information, p. 1669 - 1673 (2020/03/23)
A benzo[b]thiophene synthesis by Rh-catalyzed three-component coupling reaction of arylboronic acids, alkynes, and elemental sulfur (S8) is developed. A notable feature of this protocol is that the thienannulation (thiophene annulation) proceeds with high regioselectivity via the sequential alkyne insertion, C?H activation, and then sulfur atom transfer to the metallacycle intermediate. In a similar manner, dibenzothiophenes can be synthesized from the parent biarylboronic acids and S8. (Figure presented.).
Radical Cyclization of Arenesulfonyl Chlorides and Alkynes: A Rapid Access to π-Conjugated Benzothiophenes
Wan, Danyang,Yang, Yudong,Liu, Xingyan,Li, Mingliang,Zhao, Siling,You, Jingsong
supporting information, p. 55 - 59 (2016/01/20)
A metal-free radical cyclization of arenesulfonyl chlorides with alkynes has been developed, which provides a rapid and practical access to a variety of π-conjugated benzothiophenes with a broad reactive functional group tolerance. Furthermore, dialkynyl compounds could also undergo this transformation to give extended π-systems in good yields.
Synthesis and Reactions of Sulfenic Trifluoromethanesulfonic Anhydrides
Effenberger, Franz,Russ, Werner
, p. 3719 - 3736 (2007/10/02)
Sulfenyl halogenides 1 and 4 react with silver trifluoromethanesulfonate (2) to give aryl 3 and alkylsulfenic trifluoromethanesulfonic anhydrides 5, resp., in good yields; 3 and 5 could not be isolated because of their instability. 1H NMR spectroscopic data of 5a, b, each in dichloromethane and nitromethane, resp., are indicative of a dissoziation to adducts of alkylsulfenylium ions and the solvent.Whereas 3 do not react with aromatic compounds, addition products with diphenylacetylene, arylsulfenylvinyl trifluoromethanesulfonates 11, are formed smoothly, which under the reaction conditions immediately cyclize to give benzothiophenes 10 in excellent yields.
