107658-35-5Relevant articles and documents
The Synthesis of Biarylmonophosphonates via Palladium-Catalyzed Phosphonation, Iridium-Catalyzed C-H Borylation, Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling
Doherty, Simon,Knight, Julian G.,Tran, Tina S. T.,Alharbi, Hussam Y.,Perry, Daniel O.
, p. 398 - 413 (2022)
Abstract: The iridium-catalyzed C-H borylation of diethyl phenylphosphonate results in nonselective mono and bisborylation to afford a near statistical mixture of 3-, 3,5- and 4-boryl substituted aryl phosphonates whereas 3-substituted aryl phosphonates u
Rapid and efficient phosphonation of aryl halides catalysed by palladium under microwaves irradiation
Villemin, Didier,Jaffres, Paul-Alain,Simeon, Fabrice
, p. 59 - 63 (1997)
Diethyl arylphosphonates are efficiently and rapidly prepared from aryl halides, by a palladium catalysis, performed in a Teflon autoclave under microwave radiation generated by a commercial microwave oven.
Catalyst-free phosphorylation of aryl halides with trialkyl phosphites through electrochemical reduction
Wang, Shuai,Yang, Cheng,Sun, Shuo,Wang, Jianbo
supporting information, p. 14035 - 14038 (2019/11/25)
A catalyst-free electrochemical cross-coupling reaction of aryl halides with trialkyl phosphite has been developed. This reaction proceeds in an undivided cell with a low-cost Ni anode and a graphite cathode under mild and neutral conditions. A wide range of functional groups are well-tolerated and the phosphorylated product can be obtained on the gram scale, showing that this transformation has the potential to be a valuable method for the construction of aromatic carbon-phosphorus bonds.
Decarbonylative Phosphorylation of Carboxylic Acids via Redox-Neutral Palladium Catalysis
Liu, Chengwei,Ji, Chong-Lei,Zhou, Tongliang,Hong, Xin,Szostak, Michal
supporting information, p. 9256 - 9261 (2019/11/19)
We describe the direct synthesis of organophosphorus compounds from ubiquitous aryl and vinyl carboxylic acids via decarbonylative palladium catalysis. The catalytic system shows excellent scope and tolerates a wide range of functional groups (>50 examples). The utility of this powerful methodology is highlighted in the late-stage derivatization directly exploiting the presence of the prevalent carboxylic acid functional group. DFT studies provided insight into the origin of high bond activation selectivity and P(O)-H isomerization pathway.
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.
Nickel and palladium catalysed reaction of triethyl phosphite with aryl halides under microwave irradiation
Villemin, Didier,Elbilali, Abdelghani,Simeon, Fabrice,Jaffres, Paul-Alain,Maheut, Geraldine,Mosaddak, Mahjouba,Hakiki, Abdelhack
, p. 436 - 437 (2007/10/03)
Diethyl aryl phosphonates are efficiently and rapidly obtained from halides and triethyl phosphite without solvent. The reaction was catalysed by NiCl2 or PdCl2 (10%) under focussed microwave radiation.
Arylphosphonic acids. I. Substituent effects on their first and second dissociations
Nagarajan, K.,Shelly, Kevin P.,Perkins, R. R.,Stewart, Ross
, p. 1729 - 1733 (2007/10/02)
Thermodynamic pK1 and pK2 values of 36 arylphosphonic acids have been determined.The pK values of the meta and para compounds are correlated well by the ?n parameter, suggesting that there is little conjugation between the
