37166-46-4Relevant academic research and scientific papers
Elemental iodine-catalyzed coupling of alkynylsilanes with acid chlorides: A facile synthesis of α,β-acetylenic ketones
Yadav,Reddy,Reddy, M. Sridhar
, p. 1722 - 1724 (2003)
Alkynylsilanes undergo coupling smoothly with acid chlorides in the presence of molecular iodine under mild reaction conditions to afford the corresponding α, β-acetylenic ketones in excellent yields in a short reaction time with high selectivity.
Cascade and Effective Syntheses of Functionalized Tellurophenes
Karapala, Vamsi Krishna,Shih, Hong-Pin,Han, Chien-Chung
, p. 1550 - 1554 (2018/03/23)
A one-pot and transition-metal-catalyst-free synthetic strategy to construct functionalized tellurophenes has been developed. Substituted 1,1-dibromo-1-en-3-ynes are smoothly converted to tellurophenes with telluride salts in high yield via a series of cascade reactions through reductive debromination, hydrotelluration, nucleophilic cyclization, and aromatization. Close inspection of the results clearly showed that the reactivity of in situ prepared telluride salts are significantly influenced by the polarity of the solvent system and the electronic nature of the substituent on the enyne substrate. This method reports the first direct synthesis of 3-aryltellurophenes in high yields at room temperature. This novel reaction strategy is also found to be a promising synthetic method for multisubstituted tellurophenes and selenophenes.
A phosphine-free, atom-efficient cross-coupling reaction of triorganoindiums with acyl chlorides catalyzed by immobilization of palladium(0) in MCM-41
Miao, Jiankang,Huang, Bin,Liu, Haiyi,Cai, Mingzhong
, p. 42570 - 42578 (2017/09/11)
The first phosphine-free heterogeneous palladium(0)-catalyzed cross-coupling of triorganoindiums with acyl chlorides has been developed that proceeds smoothly in THF at 68 °C and provides a general and powerful tool for the synthesis of various valuable aryl ketones and α,β-acetylenic ketones with high atom-economy and high yield. This phosphine-free heterogeneous palladium(0) catalyst can be easily prepared from commercially available reagents and recovered by a simple filtration of the reaction solution and used for at least 10 consecutive trials without any decreases in activity. Our system not only avoids the use of phosphine ligands, but also solves the basic problem of palladium catalyst recovery and reuse.
Consecutive three- and four-component coupling-Bagley-Bohlmann-Rahtz syntheses of tri- and tetrasubstituted pyridines
Dohe, Janis,Müller, Thomas J. J.
, p. 705 - 718 (2016/07/06)
The concatenation of the modified Sonogashira alkynone synthesis and the Bagley-Bohlmann-Rahtz pyridine synthesis gives novel consecutive three- and four-component coupling-Bagley-Bohlmann-Rahtz (cBBR) syntheses of tri- and tetrasubstituted pyridines in a one-pot fashion. With these processes 15 differently substituted 3-ethoxycarbonyl 2-methylpyridines can be readily obtained in modest to moderate yields.
Friedel-crafts reactions of bis(trimethylsilyl)polyynes with acyl chlorides; a useful route to terminal-alkynyl ketones
Walton,Waugh
, p. 45 - 56 (2007/10/05)
Bis(trimethylsilyl)acetylenes, Me3Si(CC)nSiMe3, react with acyl chloride-aluminium chloride complexes, XC6H4 COCl·AlCl3 in methylene chloride at 0-20° to form the corresponding ketones XC6H4CO(CC)nSiMe3 in excellent (n = 1) or moderate (n = 2, 4) yield. Treatment of the products with aqueous methanolic borax results in virtually quantitative liberation of the terminal alkynyl ketones XC6H4CO(CC)nH. The method provides the first practical route to the ketotetraynes (n = 4) and usefully supplements existing oxidative methods for keto-monoyne and -diyne synthesis. The oxalyl chloride-aluminium chloride complex reacts with Me3SiCCSiMe3 to give the novel silyl-substituted heterocycle (I): {A figure is presented}.
