57465-40-4Relevant academic research and scientific papers
Efficient synthesis of 3-arylbutadiene sulfones using the Heck–Matsuda reaction
Asachenko, Andrey F.,Bogachev, Vasilii N.,Minaeva, Lidiya I.,Nechaev, Mikhail S.,Rzhevskiy, Sergey A.,Sterligov, Grigorii K.,Topchiy, Maxim A.
, p. 548 - 549 (2021/08/24)
An efficient and practical method for a scalable synthesis of 3-arylbutadiene sulfones deals with the ligand-free Heck–Matsuda reaction of sulfolene with aryldiazonium tetrafluoroborates followed by triethylamine-promoted double bond shift.
Redox-Divergent Construction of (Dihydro)thiophenes with DMSO
Chen, Qing-An,He, Gu-Cheng,Hu, Yan-Cheng,Ji, Ding-Wei,Liu, Heng,Zhang, Xiang-Xin,Zhao, Chao-Yang
, p. 24284 - 24291 (2021/10/08)
Thiophene-based rings are one of the most widely used building blocks for the synthesis of sulfur-containing molecules. Inspired by the redox diversity of these features in nature, we demonstrate herein a redox-divergent construction of dihydrothiophenes, thiophenes, and bromothiophenes from the respective readily available allylic alcohols, dimethyl sulfoxide (DMSO), and HBr. The redox-divergent selectivity could be manipulated mainly by controlling the dosage of DMSO and HBr. Mechanistic studies suggest that DMSO simultaneously acts as an oxidant and a sulfur donor. The synthetic potentials of the products as platform molecules were also demonstrated by various derivatizations, including the preparation of bioactive and functional molecules.
Enantioselective synthesis of chiral sulfones by ir-catalyzed asymmetric hydrogenation: A facile approach to the preparation of chiral allylic and homoallylic compounds
Zhou, Taigang,Peters, Byron,Maldonado, Matias F.,Govender, Thavendran,Andersson, Pher G.
supporting information; scheme or table, p. 13592 - 13595 (2012/10/08)
A highly efficient and enantioselective Ir-catalyzed hydrogenation of unsaturated sulfones was developed. Chiral cyclic and acyclic sulfones were produced in excellent enantioselectivities (up to 98% ee). Coupled with the Ramberg-Baecklund rearrangement, this reaction offers a novel route to chiral allylic and homoallylic compounds in excellent enantioselectivities (up to 97% ee) and high yields (up to 94%).
Competition between hetero-Diels-Alder and cheletropic additions of sulfur dioxide to 2-substituted buta-1,3-dienes. Synthesis of 2-(1-naphthyl)-and 2-(2-Naphthyl)buta-1,3-diene
Roversi, Elena,Vogel, Pierre
, p. 761 - 771 (2007/10/03)
Chloroprene (=2-chlorobuta-1,3-diene; 4b) and electron-rich dienes such as 2-methoxy-(4c), 2-acetoxy-(4d), and 2-(phenylseleno)buta-1,3-diene (4e) refused to equilibrate with the corresponding sultines 5 or 6 between - 80 and - 10° in the presence of exce
Palladium-Catalyzed Cross-Coupling Reactions of 3-Tributylstannylsulfolene
Bew, Sean P.,Sweeney
, p. 1273 - 1274 (2007/10/03)
3-Tributylstannylsulfolene (1) undergoes palladium-catalyzed cross-coupling reactions with aryl and vinyl halides, cyclohex-1-enyl triflates and acyl chlorides in moderate to excellent yield, thereby allowing rapid entry to a diverse range of 3-substitute
A facile synthesis of 3-arylbutadiene sulfones
Sengupta, Saumitra,Bhattacharyya, Sanchita
, p. 231 - 236 (2007/10/03)
3-Arylbutadiene sulfones were prepared in high yields via Heck reaction of butadiene sulfone with arenediazonium salts.
4-Bromo-2-sulfolenes. Butadienyl Cation Equivalents
Chou, Ta-shue,Hung, Su Chun,Tso, Hsi-Hwa
, p. 3394 - 3399 (2007/10/02)
4-Bromo-2-sulfolene and 4-bromo-3-methyl-2-sulfolene react with alkylcuprates to give direct substitution products, with vinyl- or phenylcuprates or sulfur-containing nucleophiles to give allylic substitution products, and with strongly basic nucleophiles to give elimination products.The allylic substitution products and the isomerized direct substitution products are precursors for substituted 1,3-butadienes.Thus, these 4-bromo-2-sulfolenes serve as butadienyl cation equivalents.
