28255-72-3Relevant academic research and scientific papers
Electron-Transfer-Induced Reactions. Termination Steps and Efficiency of the Chain Process in SRN1 Aromatic Substitutions
Amatore, Christian,Pinson, Jean,Saveant, Jean-Michel,Thiebault, Andre
, p. 6930 - 6937 (1981)
An important part of the mechanistic sequence of SRN1 aromatic substitution reactions ArX + Nu- -> ArNu + X- is a chain process, the propagation of which involves three intermediate radicals: ArX-., Ar./su
Structural variations of SnII pyridylphosphonates influenced by an uncommon Sn-N interaction
Perry, Houston,Zon, Jerzy,Law, Justin,Clearfield, Abraham
, p. 1165 - 1173 (2010)
Four new SnII phosphonates have been synthesized by hydrothermal methods, and their structures determined by single-crystal X-ray diffraction. Tin(II) 3-pyridylphosphonate, SnO3PC5H4N (I), crystallizes in P2sub
Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine
Hosseini-Sarvari, Mona,Koohgard, Mehdi
, p. 5905 - 5911 (2021/07/12)
In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed Csp2-P and Csp3-P bond formations were efficiently achieved by reacting aryl/alkylhydrazines with trialkylphosphites in the presence of air serving as an abundant oxidant. The reaction conditions tolerated a wide variety of functional groups.
Palladium-catalyzed one-pot phosphorylation of phenols mediated by sulfuryl fluoride
Zhang, Yiyuan,Chen, Wanting,Tan, Tingting,Gu, Yuang,Zhang, Shuning,Li, Jie,Wang, Yan,Hou, Wei,Yang, Guang,Ma, Peixiang,Xu, Hongtao
, p. 4588 - 4591 (2021/05/17)
We report a general palladium-catalyzed one-pot procedure for the synthesis of phosphonates, phosphinates and phosphine oxides from phenols mediated by sulfuryl fluoride. It features mild conditions, broad substrate scope, high functionality tolerance and water insensitivity. The utility of this procedure has been well demonstrated by gram-scale synthesis, sequential synthesis of click chemistry building blocks, late-stage decoration of drugs and natural products and on-DNA synthesis of phosphine oxide for a DNA-encoded library (DEL).
Photoinduced transition-metal and external photosensitizer free cross-coupling of aryl triflates with trialkyl phosphites
Dou, Qian,Geng, Li,Cheng, Bin,Li, Chao-Jun,Zeng, Huiying
supporting information, p. 8429 - 8432 (2021/09/02)
Photoinduced phosphonation of aryl triflates with trialkyl phosphites via a tandem single-electron-transfer, C-O bond cleavage and Arbuzov rearrangement process in the absence of transition-metal and external photosensitizer is reported herein. The protoc
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.
A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry
Constantin, Timothée,Juliá, Fabio,Leonori, Daniele,Sheikh, Nadeem S.
, p. 12822 - 12828 (2020/12/29)
The generation of aryl radicals from the corresponding halides by redox chemistry is generally considered a difficult task due to their highly negative reduction potentials. Here we demonstrate that α-aminoalkyl radicals can be used as both initiators and chain-carriers for the radical coupling of aryl halides with pyrrole derivatives, a transformation often employed to evaluate new highly reducing photocatalysts. This mode of reactivity obviates for the use of strong reducing species and was also competent in the formation of sp2 C-P bonds. Mechanistic studies have delineated some of the key features operating that trigger aryl radical generation and also propagate the chain process.
Cobalt catalyzed C-P bond formation by cross-coupling of boronic acids with P(O)H compounds in presence of zinc
Hicks, Ian,McTague, Jonathan,Hapatsha, Tatiana,Teriak, Rania,Kaur, Parminder
, (2020/01/31)
In our current work, we have reported the first cobalt-catalyzed cross-coupling of arylboronic acid with alkyl/aryl phosphites under mild conditions. The reaction was carried out in the presence of zinc powder as an additive and ter-pyridine as a ligand. The use of non-precious cobalt salt makes the protocol advantageous, as it is inexpensive and more abundant than the previously used methods where precious metal salts (Pd and Pt) were used. The reaction has a wide substrate scope and the products were obtained in good yields.
Electrochemical phosphorylation of arenes catalyzed by cobalt under oxidative and reductive conditions
Strekalova,Grinenko,Gryaznova,Kononov,Dolengovski,Budnikova
, p. 506 - 509 (2019/01/08)
Catalyst capable to operate in cathode and anode spaces simultaneously was found. Electrochemical regeneration of active form of catalyst Co2+bpy (1%) under oxidative as well as reductive conditions allows the C–H/P–H coupling of dialkyl-H-phos
