79238-81-6Relevant academic research and scientific papers
Total Synthesis of Indolizidine Alkaloids via Nickel-Catalyzed (4 + 2) Cyclization
Renner, Jonas,Thakur, Ashish,Rutz, Philipp M.,Cowley, Jacob M.,Evangelista, Judah L.,Kumar, Puneet,Prater, Matthew B.,Stolley, Ryan M.,Louie, Janis
supporting information, p. 924 - 928 (2020/02/04)
A Ni-catalyzed (4 + 2) cycloaddition of alkynes and azetidinones toward piperidinones was used as key reaction in the enantioselective synthesis of naturally occurring indolizidine alkaloids. The reaction benefits from the use of an easily accessible azet
Calcium carbide catalytically activated with tetra-: N -butyl ammonium fluoride for Sonogashira cross coupling reactions
Hosseini, Abolfazl,Pilevar, Afsaneh,Hogan, Eimear,Mogwitz, Boris,Schulze, Anne S.,Schreiner, Peter R.
, p. 6800 - 6807 (2017/08/22)
We report a novel method for the direct synthesis of mono- and bis-arylated alkynes utilizing catalytically activated CaC2 as the alkyne component. This fluoride-activated cross coupling reaction provides advantages over existing methods regarding operational simplicity, use of readily available starting materials, and low cost.
Total Synthesis of Lamellarin D Trimethyl Ether, Lamellarin D, and Lamellarin H
Lade, Dhanaji M.,Pawar, Amit B.,Mainkar, Prathama S.,Chandrasekhar, Srivari
, p. 4998 - 5004 (2017/05/12)
Total syntheses of three different lamellarins have been accomplished using a Ru(II)-catalyzed (3 + 2) annulation strategy to construct the central pyrrole ring. The striking features of this synthesis are the use of PEG-400 as a green solvent for the (3
Palladium-Catalyzed Domino Process: Synthesis of Symmetrical Diarylalkynes, cis- and trans-Alkenes using Lithium Acetylide as a Synthon
Krishna, Jonnada,Krishna Reddy, Alavala Gopi,Satyanarayana, Gedu
, p. 3597 - 3610 (2016/01/25)
An efficient domino protocol has been developed for the synthesis of symmetrical diarylalkynes. Notably, the method was successful in the presence of a palladium catalyst without the support of a copper co-catalyst. Significantly, the method enabled the use of the commercially available and cheap lithium acetylide ethylenediamine complex as a source of acetylene for the construction of dual C-C bonds, with a wide range of compatibility towards various substituents of the aryl bromides/iodides. Significantly, this protocol was successfully applied to the synthesis of cis- and trans-alkenes in a highly stereoselective manner in a sequential one-pot process.
Synthesis of highly functionalized 9,10-phenanthrenequinones by oxidative coupling using MoCl5
Trosien, Simon,Waldvogel, Siegfried R.
supporting information; experimental part, p. 2976 - 2979 (2012/07/27)
The strong oxidative power of molybdenum pentachloride gives rise to an efficient oxidative C-C bond formation of benzil derivatives to the corresponding 9,10-phenanthrenequinones. A highly complementary method to previous approaches was developed. The required derivatives are accessible in a modular fashion and in excellent yields. By this approach the orchid-derived natural product cypripediquinone A was synthesized for the first time.
Pd- and Ni-catalyzed cross-coupling reactions of functionalized organozinc reagents with unsaturated thioethers
Melzig, Laurin,Metzger, Albrecht,Knochel, Paul
supporting information; experimental part, p. 2948 - 2956 (2011/04/16)
A variety of unsaturated thioethers have been subjected to cross-coupling reactions with functionalized zinc reagents in the presence of a transition-metal catalyst. Three different catalytic systems based on Pd(OAc)2 or [Ni(acac)2] and the ligands S-Phos or DPE-Phos gave the best results. N-Heterocyclic thioethers based on a pyridine, pyrimidine, pyrazine, pyridazine, triazine, benzothiazole, benzoxazole, pyrrole, or quinazoline ring, as well as thiomethylacetylenes, serve as electrophiles in this cross-coupling reaction. Aryl-, heteroaryl-, benzylic, and alkylzinc halides with sensitive functionalities, such as ester, nitrile, or ketone groups react at ambient temperature with unsaturated thioethers using a Ni catalyst. The corresponding Pd-catalyzed reactions require slightly higher temperatures. Large-scale cross-coupling experiments (10-20 mmol) with N-heterocycles are also reported.
A concise palladium-catalyzed carboamination route to (±)- tylophorine
Rossiter, Lana M.,Slater, Meagan L.,Giessert, Rachel E.,Sakwa, Samuel A.,Herr, R. Jason
supporting information; experimental part, p. 9554 - 9557 (2010/03/03)
(Chemical Equation Presented) Atotal synthesis of the racemic natural product tylophorine [(±)-1] has been demonstrated using the palladium-catalyzed carboamination method developed byWolfe and co-workers. In this case, an electron-rich aryl bromide 18 wa
Heterocyclic analogs of combretastatin A-4
Vasilevsky,Davydova,Tolstikov
scheme or table, p. 1257 - 1261 (2009/05/27)
A novel route is proposed for the synthesis of heterocyclic analogs of the naturally occurring combretastatin A-4 based on the reaction of α-acetylenic ketones with polyfunctional nucleophiles (hydroxylamine, hydrazine, guanidine). Previously unknown combretastatin A-4 analogs with azole and azine bridges were obtained.
Oxidation of Aromatic Compounds. IV. Oxidation of Symmetrical Diarylacetylenes in the CF3COOH-CH2Cl2-PbO2 System. A New One-Pot Synthesis of 1,2,3,4-Tetraaryl-2-butene-1,4-diones
Rudenko, A. P.,Vasil'ev, A. V.
, p. 1360 - 1379 (2007/10/03)
Oxidation of symmetrical diarylacetylenes in the CF3COOH-CH2Cl2-PbO2 system (0-20 deg C, 1-3 h) yields 1,2,3,4-tetraaryl-2-butene-1,4-diones.According to (1)H NMR and GC-MS data the compounds synthesized have Z configuration.
AN UNUSUAL ONE STEP SYNTHESIS OF ACETYLENES
Karmarkar, Pradeep G.,Thakar, Alka A.,Wadia, Murzban S.
, p. 2301 - 2302 (2007/10/02)
Substituted nitrostyrenes on reaction with H2O2/NEt3 give 1,2 diaryl acetylenes in 30 percent yield.
