121387-01-7Relevant articles and documents
Stabilisation of carbon-supported palladium nanoparticles through the formation of an alloy with gold: Application to the Sonogashira reaction
Rossy, Cybille,Majimel, Jér?me,Fouquet, Eric,Delac?te, Cyril,Boujtita, Mohammed,Labrugère, Christine,Tréguer-Delapierre, Mona,Felpin, Fran?ois-Xavier
, p. 14024 - 14029 (2013)
A conceptually novel strategy based on the use of a bimetallic Pd-Au/C catalyst and its application to the Sonogashira reaction under ligand- and additive-free conditions was studied. Pd(OAc)2 and charcoal were dispersed in MeOH (100 mL). Then, hydrogen gas was bubbled through the solution for 5 min to remove the oxygen. The resulting mixture was stirred for 12 h at 25°C under H2. The catalyst was filtered under Millipore membrane washed with MeOH and dried under vacuum. ICP analyses were performed on the filtrate to verify the final Pd metal loading on carbon to be 5%wt. Detailed HR-TEM analyses established that the aggregation phenomenon can be considerably slowed down thanks to the stabilising, but catalytically inactive, gold atoms. Although X-ray photoelectron spectroscopy (XPS) analysis identified Au0 and Pd0 as the major species present in the as-prepared material, some ionic palladium (19 at.%) was also detected
Ortho Effects in Organic Molecules on Electron Impact. Part 16. Novel Oxygen Transfers from the Nitro Group to Acetylenic Carbons in 2-Nitrophenylacetylenes
Ramana, D. V.,Krishna, N. V. S. Rama
, p. 66 - 69 (1989)
Oxygen transfers to both acetylene carbons are noticed in parallel fragmentation pathways during the electron impact induced decompositions of 2-nitrodiphenylacetylene.The oxygen transfer to β-acetylenic carbon leads to the most abundant ion corresponding
Palladium-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with arylboronic acids
Feng, Chao,Loh, Teck-Peng
, p. 4779 - 4781 (2010)
A highly efficient and mild palladium-catalyzed decarboxylative cross-coupling of aryl boronic acids and alkynyl carboxylic acids for the synthesis of unsymmetrical substituted alkynes is described for the first time.
On the peculiar recycling properties of charcoal-supported palladium oxide nanoparticles in Sonogashira reactions
Rossy, Cybille,Majimel, Jér?me,Delapierre, Mona Tréguer,Fouquet, Eric,Felpin, Fran?ois-Xavier
, p. 157 - 162 (2014)
The enhanced recycling properties of 5% PdO NPs/C compared to 5% Pd NPs/C catalyst for the Sonogashira reaction has been unveiled. A simple preparation procedure for 5% Pd NPs/C and 5% PdO NPs/C catalysts is described along with their extensive characteri
Electrochemically Enabled Selenium Catalytic Synthesis of 2,1-Benzoxazoles fromo-Nitrophenylacetylenes
Wang, Lin-Wei,Feng, Yu-Feng,Lin, Hong-Min,Tang, Hai-Tao,Pan, Ying-Ming
, p. 16121 - 16127 (2021/03/09)
The study reported an electrochemically mediated method for the preparation of 2,1-benzoxazoles fromo-nitrophenylacetylenes. Different from the traditional electrochemical reduction of nitro to nitroso, the nitro group directly underwent a cyclization rea
Synthesis of Aryl Alkynes via Copper Catalyzed Decarboxylative Alkynylation of 2-Nitrobenzoic Acids
Yu, Yongqi,Chen, Xiang,Wu, Qianlong,Liu, Da,Hu, Liang,Yu, Lin,Tan, Ze,Gui, Qingwen,Zhu, Gangguo
supporting information, p. 8556 - 8566 (2018/06/29)
An efficient protocol for the synthesis of internal aryl alkynes was achieved via Cu-catalyzed decarboxylative cross-coupling reactions, and to the best of our knowledge, this is the first example of a Cu-catalyzed decarboxylative alkynylation of benzoic acids with terminal alkynes. This approach utilizes simple Cu salt as catalyst and O2, an abundant, clean, and green material, as the oxidant. The reaction tolerates various functional groups, and a variety of internal aryl alkynes were synthesized in 46-83% yields.
Pd/Cu-free Heck and Sonogashira cross-coupling reaction by Co nanoparticles immobilized on magnetic chitosan as reusable catalyst
Hajipour, Abdol R.,Rezaei, Fatemeh,Khorsandi, Zahra
supporting information, p. 1353 - 1361 (2017/08/18)
Chitosan (CS) is a porous, self-standing, nanofibrillar microsphere that can be used as a metal carrier. Amino groups on CS enable to modulate cobalt coordination using a safe organic ligand (methyl salicylate). This catalyst efficiently promotes Heck cross-coupling of a large library of functional substrates under mild and sustainable conditions (polyethylene glycol as solvent at 80 °C in a short time (1 h)). The cobalt complex was also used as a heterogeneous, efficient, inexpensive, and green catalyst for Sonogashira cross-coupling reactions. The reactions of various aryl halides and phenylacetylene provided the corresponding products in moderate to good yields. More importantly, this phosphine, copper, and palladium-free catalyst was stable under the reaction conditions and could be easily reused using an external magnet for at least five successive runs without a discernible decrease in its catalytic activity.
One-Pot Synthesis of Indole Derivatives from the Reaction of Nitroalkynes and Alkynes via a Mercury-Carbene Intermediate
Zheng, Min,Chen, Kai,Zhu, Shifa
, p. 4173 - 4182 (2017/09/13)
The cyclization of nitroalkyne catalyzed by Hg(OTf) 2 to produce the corresponding benzo[ c ]isoxazole in excellent yields with high selectivity is reported. On the basis of this strategy, a one-pot method to synthesize indole derivatives has been developed. In this transformation, two Hg-carbene intermediates are proposed to be involved..
Gold(i)-catalyzed synthesis of 2-substituted indoles from 2-alkynylnitroarenes with diboron as reductant
Fu, Wenqiang,Yang, Kai,Chen, Jinglong,Song, Qiuling
, p. 8354 - 8360 (2017/10/19)
An efficient method for the synthesis of 2-substituted indoles via a diboron/base promoted tandem reductive cyclization of o-alkynylnitroarene under Au catalysis conditions has been disclosed. This reaction is efficient and convenient, affording 2-substituted indoles with broad functional groups tolerance and excellent yields.
2-Aryl-3H-indol-3-ones: Synthesis, electrochemical behaviour and antiplasmodial activities
Najahi, Ennaji,Valentin, Alexis,Fabre, Paul-Louis,Reybier, Karine,Nepveu, Fran?oise
, p. 269 - 274 (2014/04/17)
The synthesis of indolone derivatives and their antiplasmodial activity in vitro against Plasmodium falciparum at the blood stage are described. The 2-aryl-3H-indol-3-ones were synthesized via deoxygenation of indolone-N-oxides. Electrochemical behaviour, antiplasmodial activity and cytotoxicity on human tumor cell lines were compared to those of indolone-N-oxides. The antiplasmodial IC50 (concentrations at 50% inhibition) of these compounds ranged between 49 and 1327 nM. Among them, the 2-(4-dimethylaminophenyl)-5-methoxy- indol-3-one, 7, had the best antiplasmodial activity in vitro (IC50 = 49 nM; FcB1 strain) and selectivity index (SI (CC50 MCF7/IC 50 FcB1) = 423.4). Thus, the hits identified in this deoxygenated series correspond to their structural homologs in the N-oxide series with comparable electrochemical behaviour at the nitrogen-carbon double bond.
