69381-90-4Relevant academic research and scientific papers
Visible-light and thermal driven double hydrophosphination of terminal alkynes using a commercially available iron compound
Ackley, Brandon J.,Pagano, Justin K.,Waterman, Rory
supporting information, p. 2774 - 2776 (2018/03/21)
A commercially available iron compound, [CpFe(CO)2]2 (1) (Cp = η5-C5H5), is an efficient catalyst for the double hydrophosphination of terminal aryl alkynes with diphenylphosphine under visible light irradiation or thermal conditions with a reduction of reaction times of up to two orders of magnitude for some substrates over literature reports. The 1,2-bis(diphenylphosphino)ethane products generated in these reactions are readily isolated in high yields.
1,1-Diphosphines and divinylphosphines via base catalyzed hydrophosphination
Coles,Mahon,Webster
supporting information, p. 10443 - 10446 (2018/09/21)
A catalytic hydrophosphination route to 1,1-diphosphines is yet to be reported: these narrow bite angle pro-ligands have been used to great effect as ligands in homogeneous catalysis. We herein demonstrate that terminal alkynes readily undergo double hydrophosphination with HPPh2 and catalytic potassium hexamethyldisilazane (KHMDS) to generate 1,1-diphosphines. A change to H2PPh leads to the formation of P,P-divinyl phosphines.
Sequential Addition of Phosphine to Alkynes for the Selective Synthesis of 1,2-Diphosphinoethanes under Catalysis. Well-Defined NHC-Copper Phosphides vs in Situ CuCl2/NHC Catalyst
Yuan, Jia,Zhu, Lizhao,Zhang, Jianying,Li, Jianfeng,Cui, Chunming
supporting information, p. 455 - 459 (2017/04/26)
The well-defined NHC-copper phosphides [(NHC)CuPPh2]3 (1, NHC = 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (IiPr); 2, NHC = N,N-di-tert-butylimidazol-2-ylidene (ItBu)) have been prepared by the reaction of simple copper halides with HPPh2 in the presence of N-heterocyclic carbenes (NHCs). Complexes 1 and 2 enabled catalytic double hydrophosphination of alkyl and aryl terminal alkynes to yield 1,2-diphosphinoethanes selectively in good yields. On the basis of these results, the most efficient and pratical in situ CuCl2/NHC catalyst has been developed. It catalyzes the selective double hydrophosphination of the alkynes with high efficiency and a wide substrate scope and exhibits even better performance than the well-defined NHC-Cu phosphides. The mechanistic studies disclosed that the formation of a copper acetylide in the catalytic cycle played an important role in the acceleration of the catalytic process.
Copper-Catalyzed Vicinal Diphosphination of Styrenes: Access to 1,2-Bis(diphenylphosphino)ethane-Type Bidentate Ligands from Olefins
Okugawa, Yuto,Hirano, Koji,Miura, Masahiro
supporting information, p. 13558 - 13561 (2016/10/21)
A copper/N-heterocyclic carbene (NHC) catalyzed oxidative vicinal diphosphination of styrenes with diphenyl(trimethylsilyl)phosphine proceeds in the presence of LiOtBu and a pyridine N-oxide/MnO2combined oxidant to deliver the corresponding 1,2-bis(diphenylphosphino)ethanes (DPPEs) in good yields. The present copper catalysis can provide access to the DPPE-type ligands directly from the relatively simple alkenes.
Double hydrophosphination of alkynes promoted by rhodium: The key role of an N-heterocyclic carbene ligand
Di Giuseppe, Andrea,De Luca, Roberto,Castarlenas, Ricardo,Pérez-Torrente, Jesús J.,Crucianelli, Marcello,Oro, Luis A.
supporting information, p. 5554 - 5557 (2016/05/09)
The regioselective double hydrophosphination of alkynes mediated by rhodium catalysts is presented. The distinctive stereoelectronic properties of the NHC ligand prevent the catalyst deactivation by diphosphine coordination thereby allowing for the closing of a productive catalytic cycle.
Synthesis of vinylphosphines and unsymmetric diphosphines: Iron-catalyzed selective hydrophosphination reaction of alkynes and vinylphosphines with secondary phosphines
Itazaki, Masumi,Katsube, Shinya,Kamitani, Masahiro,Nakazawa, Hiroshi
, p. 3163 - 3166 (2016/02/20)
Iron complex-catalyzed regioselective single hydrophosphination of terminal arylalkynes with secondary phosphines was achieved. Unsymmetric 1,2-bis(phosphino)ethanes with different phosphino groups were obtained by using our catalytic systems. The structu
Switchable ethylene tri-/tetramerization with high activity: Subtle effect presented by backbone-substituent of carbon-bridged diphosphine ligands
Zhang, Jun,Wang, Xiao,Zhang, Xuejun,Wu, Weijie,Zhang, Gengtao,Xu, Sheng,Shi, Min
, p. 2311 - 2317 (2013/10/22)
The effect of backbone-substituent of carbon-bridged diphosphine ligands of the types {Ph2PCH(R)CH2PPh2} and {Ph 2PC(R)iCHPPh2} on the catalyst performance in ethylene oligomerization has been explore
Regioselective double hydrophosphination of terminal arylacetylenes catalyzed by an iron complex
Kamitani, Masahiro,Itazaki, Masumi,Tamiya, Chihiro,Nakazawa, Hiroshi
supporting information; experimental part, p. 11932 - 11935 (2012/09/08)
The first catalytic double hydrophosphination of alkynes was achieved by reaction with diarylphosphines in the presence of an iron catalyst. The double hydrophosphination proceeded regioselectively and effectively for various secondary arylphosphines and
Facile synthesis of chelating bisphosphine oxides and bisphosphines via palladium-catalyzed bishydrophosphinylation reactions
Allen Jr., Aberdeen,Ma, Ling,Lin, Wenbin
, p. 3707 - 3710 (2007/10/03)
A series of functional bisphosphosphine oxides were synthesized in good yields via new Pd-catalyzed bis-hydrophosphinylation reactions of terminal alkynes and diphenylphosphine oxide. The resulting bisphosphine oxides were reduced to their corresponding b
ACETYLENIC HYDROCARBONS AND VINYL HALIDES IN THE ALKYLATION OF PH ACIDS UNDER CONDITIONS OF PHASE-TRANSFER CATALYSIS OR IN SUPERBASIC MEDIUM
Khachatryan, R. A.,Grigoryan, N. Yu.,Indzhikyan, M. G.
, p. 1134 - 1138 (2007/10/02)
By the reaction of nonactivated acetylenes with diphenylphosphine under phase-transfer catalysis or in superbasic medium the corresponding mono- and diphosphines were obtained, whereas with diphenylphosphine oxide only bis(phosphine oxides) were formed.Diphenylphosphine was found to react with 1,1- and 1,2-dichloroethenes, as well as with 1,1,2-trichloroethane, yielding 1,2-bis(diphenylphosphino)ethene.The reactions of E-1-chloro-2-phenyl- and 1-chloro-1-phenylethenes with diphenylphosphine under similar conditions lead either to E-1-diphenylphosphino-2-phenylethene or to bisphosphine with a ratio of reactants of 1:1 or 1:2 respectively.Diphenylphosphine oxide gives bis(phosphine oxides) in all the above cases.Stereochemistry and mechanism of the reactions are discussed.
