17067-92-4Relevant articles and documents
Practical protocol for the palladium-catalyzed synthesis of arylphosphonates from bromoarenes and diethyl phosphite
Goo?en, Lukas J.,Dezfuli, Mohammad K.
, p. 445 - 448 (2005)
A greatly improved, reliable protocol for the palladium-catalyzed cross-coupling of dialkyl phosphites with aryl bromides has been developed. The use of an alcoholic solvent was the key to high yields in the synthesis of a broad variety of arylphosphonate
Microwave assisted P–C coupling reactions without directly added P-ligands
Henyecz, Réka,Huszár, Bianka,Keglevich, Gy?rgy,Mucsi, Zoltán
, (2021/12/24)
Our group introduced a green protocol for the Pd(OAc)2- or NiCl2-catalyzed P–C coupling reaction of aryl halides and various > P(O)H-compounds under MW conditions without directly added P-ligands. The reactivity of a few aryl derivatives in the Pd(OAc)2-catalyzed Hirao reaction was also studied. An induction period was observed in the reaction of bromobenzene and diphenylphosphine oxide. Finally, the less known copper(I)-promoted P–C coupling reactions were investigated experimentally. The mechanism was explored by quantum chemical calculations.
Nickel-Catalyzed Phosphorylation of Tosylates
Li, Chun-jing
, p. 725 - 730 (2020/06/30)
Abstract: Four new bidentate phosphine ligands have been synthesized, characterized and evaluated in Ni-catalyzed C–P coupling reaction. The readily available and inexpensive highly active sulfonate Ni(cod)2-L8 catalyzes the reaction leading to
Potent Reductants via Electron-Primed Photoredox Catalysis: Unlocking Aryl Chlorides for Radical Coupling
Chernowsky, Colleen P.,Cowper, Nicholas G. W.,Wickens, Zachary K.,Williams, Oliver P.
supporting information, (2020/02/04)
We describe a new catalytic strategy to transcend the energetic limitations of visible light by electrochemically priming a photocatalyst prior to excitation. This new catalytic system is able to productively engage aryl chlorides with reduction potentials hundreds of millivolts beyond the potential of Na0 in productive radical coupling reactions. The aryl radicals produced via this strategy can be leveraged for both carbon-carbon and carbon-heteroatom bond-forming reactions. Through direct comparison, we illustrate the reactivity and selectivity advantages of this approach relative to electrolysis and photoredox catalysis.
Visible Light-Driven, Photocatalyst-Free Arbuzov-Like Reaction via Arylazo Sulfones
Qiu, Di,Lian, Chang,Mao, Jinshan,Ding, Yi,Liu, Zerong,Wei, Liyan,Fagnoni, Maurizio,Protti, Stefano
, p. 5239 - 5244 (2019/11/11)
A visible light-induced formation of Aryl-Phosphorous bonds starting from arylazo sulfones and triaryl (or trialkyl)phosphites in the absence of any photoredox catalyst and any additives was developed. This reaction showed a broad substrate scope and afforded (hetero)aryl phosphonates in good yields and in up to the gram scale.
Practical C–P bond formation via heterogeneous photoredox and nickel synergetic catalysis
Koranteng, Ernest,Liu, Yi-Yin,Liu, Si-Yue,Wu, Qiang-Xian,Lu, Liang-Qiu,Xiao, Wen-Jing
, p. 1841 - 1846 (2019/11/11)
An efficient C–P bond formation reaction was developed by virtue of the synergetic catalysis strategy by merging heterogeneous photocatalysis and nickel catalysis. This platform utilizing cadmium sulfide semiconductors as heterogeneous photocatalysts and
Nickel-Catalyzed Electrochemical Phosphorylation of Aryl Bromides
Bai, Ya,Liu, Nian,Wang, Shutao,Wang, Siyu,Ning, Shulin,Shi, Lingling,Cui, Lili,Zhang, Zhuoqi,Xiang, Jinbao
supporting information, p. 6835 - 6838 (2019/09/30)
A nickel-catalyzed electrochemical cross-coupling reaction of aryl bromides with dialkyl phosphites, ethyl phenylphosphinate, and diphenylphosphine oxide has been developed. This reaction utilizes a simple undivided cell with inexpensive carbon electrodes to synthesize aryl phosphonates, aryl phosphinates, and arylphosphine oxides at room temperature. This protocol provides a mild and efficient route for the construction of C-P bond in moderate to high yields with broad substrate scope.
Sensitization-Initiated Electron Transfer for Photoredox Catalysis
Ghosh, Indrajit,Shaikh, Rizwan S.,K?nig, Burkhard
supporting information, p. 8544 - 8549 (2017/07/11)
Photosynthetic organisms exploit antenna chromophores to absorb light and transfer excitation energy to the reaction center where redox reactions occur. In contrast, in visible-light chemical photoredox catalysis, a single species (i.e., the photoredox catalyst) absorbs light and performs the redox chemistry. Mimicking the energy flow of the biological model, we report a two-center photoredox catalytic approach in which the tasks of light energy collection and electron transfer (i.e., redox reactions) are assigned to two different molecules. Ru(bpy)3Cl2 absorbs the visible light and transfers the energy to polycyclic aromatic hydrocarbons that enable the redox reactions. This operationally simple sensitization-initiated electron transfer enables the use of arenes that do not absorb visible light, such as anthracene or pyrene, for photoredox applications. We demonstrate the merits of this approach by the reductive activation of chemical bonds with high reduction potentials for carbon–carbon and carbon–heteroatom bond formations.
Visible-Light photo-Arbuzov reaction of aryl bromides and trialkyl phosphites yielding aryl phosphonates
Shaikh, Rizwan S.,Düsel, Simon J.S.,K?nig, Burkhard
, p. 8410 - 8414 (2018/05/23)
Aryl phosphonates are functional groups frequently found in pharmaceutical and crop protection agents. For their synthesis via C?P bond formation typically transition-metal-catalyzed reactions are used. We report a visible-light photo-Arbuzov reaction as an efficient, mild, and metal-free alternative. Rhodamine 6G (Rh.6G) is used as the photocatalyst, generating aryl radicals under blue light. Coupling of the radicals with a wide range of trivalent phosphites gives aryl phosphonates in good to very good isolated yields. The mild reaction conditions allow the introduction of a phosphonate group into complex and sensitive pharmaceutically active molecules such as benzodiazepams and nicergoline by the activation of a carbon?halogen bond.
Palladium-Catalyzed Phosphorylation of Aryl Mesylates and Tosylates
Fu, Wai Chung,So, Chau Ming,Kwong, Fuk Yee
supporting information, p. 5906 - 5909 (2015/12/11)
The first general palladium catalyst for the phosphorylation of aryl mesylates and tosylates is reported. The newly developed system exhibits excellent functional group compatibility. For instance, free amino, keto, ester, and amido groups, as well as het
