10413-38-4Relevant academic research and scientific papers
Enantioselective hydroarylation or hydroalkenylation of benzo[b]thiophene 1,1-dioxides with organoboranes
Hu, Fangdong,Jia, Jie,Li, Ximing,Xia, Ying
supporting information, p. 896 - 901 (2021/02/01)
An efficient protocol for the asymmetric hydroarylation and hydroalkenylation of benzo[b]thiophene 1,1-dioxides with organoboranes has been developed. The combination of a rhodium(I) precatalyst and a chiral diene ligand constitutes the catalytic system, which enables the facile synthesis of 2,3-dihydrobenzo[b]thiophene 1,1-dioxides in good yields with high enantioselectivities. The merging of this asymmetric hydroarylation with the downstream alkylations delivers 2,3-dihydrobenzo[b]thiophene 1,1-dioxides that contain two continuous quaternary stereocenters with high enantioselectivities in a diastereodivergent manner.
Addition Reactions of Benzothiophen. Part 1. Self-addition and Addition of Simple Aromatic Hydrocarbons
Clark, Peter David,Clarke, Kenneth,Ewing, David F.,Scrowston, Richard M.
, p. 677 - 685 (2007/10/02)
Benzothiophen undergoes facile addition reactions across the 2,3-bond when treated with aluminium chloride in an appropriate solvent at 0 or 20 deg C.In carbon disulphide or dichloromethane, it undergoes self-addition to give two or more of the four possible 2- or 3-(2- or 3-benzothienyl)2,3-dihydrobenzothiophens (3)-(6).In the presence of an aromatic solvent, the dimerization reaction just mentioned predominates at low temperatures (0 deg C or below), or at room temperature if the solvent is benzene, chlorobenzene, t-butylbenzene, isopropylbenzene, or 1,3,5-trimethylbenzene.At room temperature, in toluene, ethylbenzene, and 1,2- or 1,4-dimethylbenzene, solvent addition occurs to give a mixture of the corresponding 2- and 3-aryl-2,3-dihydrobenzenethiophens.At 80 deg C, benzene and toluene give the fully aromatic 2-arylbenzothiophen.The reactions are discussed in terms of an ionic mechanism involving protonation of benzothiophen by moist aluminium chloride and reaction of the resulting electrophile with benzothiophen or with an aromatic substrate.
