28036-01-3Relevant academic research and scientific papers
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
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.
Manganese-Catalyzed and Mediated Synthesis of Arylphosphinates and Related Compounds
Berger, Olivier,Montchamp, Jean-Luc
, p. 9239 - 9256 (2019/08/12)
The free-radical arylation of H-phosphinates and related compounds was examined. A practical catalytic process with the air as the oxidant could not be found. However, an inexpensive and robust methodology was developed, using catalytic Mn(II) as the radi
Visible-Light-Mediated Metal-Free Synthesis of Aryl Phosphonates: Synthetic and Mechanistic Investigations
Lecroq, William,Bazille, Pierre,Morlet-Savary, Fabrice,Breugst, Martin,Lalevée, Jacques,Gaumont, Annie-Claude,Lakhdar, Sami
supporting information, p. 4164 - 4167 (2018/07/29)
This work describes a straightforward access to a large variety of aryl phosphonates by the simple combination of diaryliodonium salts with phosphites in the presence of a base and under visible-light illumination. The reaction proceeds smoothly, tolerates various functionalities, and was applied for the synthesis of pharmaceutically relevant compounds. Mechanistic investigations, including EPR, NMR, and DFT calculations, support the postulated reaction mechanism.
Visible-Light-Induced External Oxidant-Free Oxidative Phosphonylation of C(sp2)-H Bonds
Niu, Linbin,Liu, Jiamei,Yi, Hong,Wang, Shengchun,Liang, Xing-An,Singh, Atul K.,Chiang, Chien-Wei,Lei, Aiwen
, p. 7412 - 7416 (2017/11/14)
Considering the synthetic value of phosphonates, developing powerful catalytic methods for the phosphonylation of C(sp2)-H bonds is important. Herein, we achieve a visible-light-induced external oxidant-free oxidative phosphonylation of C(spsu
Pd-catalyzed P-arylation of triarylantimony dicarboxylates with dialkyl H-phosphites without a base: Synthesis of arylphosphonates
Matsumura, Mio,Dong, Yuqiang,Kakusawa, Naoki,Yasuike, Shuji
, p. 130 - 133 (2015/02/19)
The reaction of triarylantimony diacetates [Ar3Sb(OAc)2] with dialkyl H-phosphites [H-PO(OR)2] in the presence of a Pd(PPh3)4 (5 mol%) catalyst led to the formation of arylphosphonates in moderate to excellent yield under base-free conditions. This reaction is the first example of carbon-phosphorus bond formation by using an organoantimony compound as a pseudo-halide.
Metal-free azaphosphaannulation of phosphonamides through intramolecular oxidative C-N bond formation
Kim, Yea Rin,Cho, Seungyoon,Lee, Phil Ho
supporting information, p. 3098 - 3101 (2014/06/23)
We report an efficient metal-free azaphosphaannulation of a myriad of phosphonamides through intramolecular oxidative C-N bond formation using PhI(OAc)2 and iodine in acetonitrile under air, thus leading to the formation of benzazaphosphol-3-on
Manganese-Mediated Intermolecular Arylation of H-Phosphinates and Related Compounds
Berger, Olivier,Montchamp, Jean-Luc
supporting information, p. 12385 - 12388 (2015/02/19)
The intermolecular radical functionalization of arenes with aryl and alkyl H-phosphinate esters, as well as diphenylphosphine oxide and H-phosphonate diesters, is described. The novel catalytic MnII/excess MnIVsystem is a convenient
Phosphonation of arenes with dialkyl phosphites catalyzed by Mn(II)/Co(II)/O2 redox couple
Kagayama, Takashi,Nakano, Atsushi,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 407 - 409 (2007/10/03)
Arylphosphonates were first synthesized through a catalytic phosphonation of various arenes with dialkyl phosphites under the influence of an Mn(OAc) 2/Co(OAc)2/O2 redox couple. For instance, the reaction of benzene with d
A direct and new convenient oxidation: Synthesis of substituted arylphosphonates from aromatics
Simeon, Fabrice,Jaffres, Paul-Alain,Villemin, Didier
, p. 10111 - 10118 (2007/10/03)
An easy synthesis of aryl phosphonates by oxidation from aryldichlorophosphines with iodine in good yields is described. Aryldichlorophosphines are obtained by reaction of phosphorous trichloride with some aromatics in presence of various Lewis acids. BiCl3 and Bi(OTf)3 are used for the first time and bismuth trichloride is, for the first time in the case of anisole or thioanisole phosphonylation, used as a true regenerable Lewis acid catalyst in a reaction of direct phosphonylation of aromatics.
