161374-29-4Relevant academic research and scientific papers
Catalytic Generation of Rhodium Silylenoid for Alkene-Alkyne-Silylene [2 + 2 + 1] Cycloaddition
Ohmura, Toshimichi,Sasaki, Ikuo,Suginome, Michinori
, p. 1649 - 1653 (2019/03/20)
An alkene-alkyne-silylene [2 + 2 + 1] cycloaddition takes place in the rhodium-catalyzed reaction of 1,6-enynes with borylsilanes bearing an alkoxy group on the silicon atoms, which react as synthetic equivalents of silylene. The reaction proceeds efficiently in 1,2-dichloroethane at 80-110 °C in the presence of a rhodium catalyst bearing bis(diphenylphosphino)methane (DPPM) as a ligand to afford 1-silacyclopent-2-enes in good to high yields.
Atom-Economical Ni-Catalyzed Diborylative Cyclization of Enynes: Preparation of Unsymmetrical Diboronates
Cabrera-Lobera, Natalia,Quirós, M. Teresa,Brennessel, William W.,Neidig, Michael L.,Bu?uel, Elena,Cárdenas, Diego J.
supporting information, p. 6552 - 6556 (2019/08/20)
We report a Ni-catalyzed diborylative cyclization of enynes that affords carbo- and heterocycles containing both alkyl- and alkenylboronates. The reaction is fully atom-economical, shows a broad scope, and employs a powerful and inexpensive catalytic Ni-b
Iron-Catalyzed Hydroborylative Cyclization of 1,6-Enynes
Cabrera-Lobera, Natalia,Rodríguez-Salamanca, Patricia,Nieto-Carmona, Juan C.,Bu?uel, Elena,Cárdenas, Diego J.
supporting information, p. 784 - 788 (2017/11/29)
We report first Fe-catalyzed hydroborylative cyclization reaction. The process provides one C?C and one C?B bond in a single operation and shows a wide scope, allowing the formation of carbo- and heterocycles containing a homoallylic boryl unit that can b
A New Approach to Non-Coordinating Anions: Lewis Acid Enhancement of Porphyrin Metal Centers in a Zwitterionic Metal-Organic Framework
Johnson, Jacob A.,Petersen, Brenna M.,Kormos, Attila,Echeverría, Elena,Chen, Yu-Sheng,Zhang, Jian
supporting information, p. 10293 - 10298 (2016/09/03)
We describe a new strategy to generate non-coordinating anions using zwitterionic metal-organic frameworks (MOFs). By assembly of anionic inorganic secondary building blocks (SBUs) ([In(CO2)4]-) with cationic metalloporphyrin-based organic linkers, we prepared zwitterionic MOFs in which the complete internal charge separation effectively prevents the potential binding of the counteranion to the cationic metal center. We demonstrate the enhanced Lewis acidity of MnIII- and FeIII-porphyrins in the zwitterionic MOFs in three representative electrocyclization reactions: [2 + 1] cycloisomerization of enynes, [3 + 2] cycloaddition of aziridines and alkenes, and [4 + 2] hetero-Diels-Alder cycloaddition of aldehydes with dienes. This work paves a new way to design functional MOFs for tunable chemical catalysis.
Secondary phosphine oxide-gold(I) complexes and their first application in catalysis
Schroeder, Felix,Tugny, Coralie,Salanouve, Elise,Clavier, Herve,Giordano, Laurent,Moraleda, Delphine,Gimbert, Yves,Mouries-Mansuy, Virginie,Goddard, Jean-Philippe,Fensterbank, Louis
supporting information, p. 4051 - 4056 (2014/10/15)
A series of new secondary phosphine oxide (SPO)-gold(I) complexes have been synthesized and characterized by X-ray crystallography. Complexes exhibited dimeric structures interconnected by O-H···Cl hydrogen bonds. Their first use in homogeneous catalysis
Pauson-Khand reactions in a photochemical flow microreactor
Asano, Keisuke,Uesugi, Yuki,Yoshida, Jun-Ichi
supporting information, p. 2398 - 2401 (2013/06/27)
Pauson-Khand reactions were achieved at ambient temperature without any additive using a photochemical flow microreactor. The efficiency of the reaction was better than that in a conventional batch reactor, and the reaction could be operated continuously for 1 h.
(Pentamethylcyclopentadienyl)iridium dichloride dimer {[IrCp*Cl 2]2}: A novel efficient catalyst for the cycloisomerizations of homopropargylic diols and N-tethered enynes
Benedetti, Erica,Simonneau, Antoine,Hours, Alexandra,Amouri, Hani,Penoni, Andrea,Palmisano, Giovanni,Malacria, Max,Goddard, Jean-Philippe,Fensterbank, Louis
supporting information; experimental part, p. 1908 - 1912 (2011/10/05)
(Pentamethylcyclopentadienyl)iridium dichloride dimer {[IrCp*Cl 2]2}-catalyzed hydroalkoxylation of bis-homopropargylic alcohols provides an efficient access to dioxabicyclo[2.2.1]ketals. The cycloisomerizations proceed under mild conditions, with low catalytic loadings and short reaction times. This new protocol involving an Ir(III) catalyst also promoted the cycloisomerization of nitrogen-tethered 1,6-enynes to give azabicyclo[4.1.0]heptenes, enhancing the synthetic potential of our method. Copyright
Iron-catalyzed, hydrogen-mediated reductive cyclization of 1,6-enynes and diynes: Evidence for bis(imino)pyridine ligand participation
Sylvester, Kevin T.,Chirik, Paul J.
supporting information; experimental part, p. 8772 - 8774 (2009/12/04)
(Chemical Equation Presented) The bis(imino)pyridine iron dinitrogen complex (iPrPDI)Fe(N2)2 catalyzes the hydrogen-mediated reductive cyclization of enynes and diynes with turnover frequencies comparable to those of established precious metal catalysts. Amino, oxygenated, and carbon-based substrates are readily cyclized to the corresponding hetero- and carbocycles with 5 mol % iron and 4 atm H2 at 23°C. Stoichiometric reactions between selected substrates and the iron compound under a N2 atmosphere established transfer dehydrogenation from an isopropyl aryl substituent to either the enyne or diyne substrate. In situ monitoring of the catalytic reaction by 1H NMR spectroscopy coupled with deuterium labeling experiments established rapid cyclization followed by turnoverlimiting hydrogenation. Copyright
Microwave-assisted rhodium-complex-catalyzed cascade decarbonylation and asymmetric Pauson-Khand-type cyclizations
Hang, Wai Lee,Lai, Na Lee,Chan, Albert S. C.,Fuk, Yee Kwong
supporting information; experimental part, p. 3403 - 3406 (2009/04/07)
Microwave-assisted Rh-diphosphane-complex-catalyzed dual catalysis is reported. This cooperative process provides [2+2+1] cycloadducts by sequential decarbonylation of aldehyde or formate and carbonylation of enynes within a short period of time. Various
Gold(l)-catalyzed cascade cyclization reaction: Highly regio- and diastereoselective intermodular addition of water and alcohols to epoxy alkynes
Dai, Lun-Zhi,Qi, Ming-Juan,Shi, Yong-Ling,Liu, Xu-Guang,Shi, Min
, p. 3191 - 3194 (2008/02/11)
We have developed a novel access to ketal skeletons through a highly regio- and diastereoselective intermolecular addition of water and alcohols to alkynyl epoxides catalyzed by goid(l). This procedure involves a domino three-membered ring-opening, 6-exo-
