2511-09-3Relevant academic research and scientific papers
Palladium-Catalyzed Domino Cyclization/Phosphorylation of gem-Dibromoolefins with P(O)H Compounds: Synthesis of Phosphorylated Heteroaromatics
Chen, Chen,Ding, Jie,Liu, Liying,Huang, Yujie,Zhu, Bolin
supporting information, p. 200 - 205 (2021/10/29)
We presented a palladium-catalyzed domino cyclization/phosphorylation of gem-dibromoolefins, which utilize H-phosphinates and secondary phosphine oxides as the phosphine sources, respectively. A variety of phosphorylated heteroaromatics were obtained in m
A facile and practical preparation ofP-chiral phosphine oxides
Xu, Ronghua,Gao, Zhenhua,Yu, Yiteng,Tang, Yehua,Tian, Duanshuai,Chen, Tian,Chen, Yibing,Xu, Guangqing,Shi, Enxue,Tang, Wenjun
supporting information, p. 3335 - 3338 (2021/04/07)
A practical and cost-effective synthetic method ofP-chiral diarylalkyl, aryldialkyl, and triaryl phosphine oxides by using readily available chiral diphenyl-2-pyrrolidinemethanol as the auxiliary is developed. The long-standing racemization issue during s
Stereo- And Regioselective cis-Hydrophosphorylation of 1,3-Enynes Enabled by the Visible-Light Irradiation of NiCl2(PPh3)2
Hou, Hong,Zhou, Bing,Wang, Jiawei,Zhao, Dengyang,Sun, Duhao,Chen, Xiaoyun,Han, Ying,Yan, Chaoguo,Shi, Yaocheng,Zhu, Shaoqun
supporting information, p. 2981 - 2987 (2021/05/05)
Described herein is a stereo- and regioselective cis-hydrophosphorylation reaction of the internal alkyne of 1,3-enynes that accesses various 1,3-dienes in good isolated yields. The visible-light irradiation of NiCl2(PPh3)2 allows the generation of highly reactive nickel(II)-phosphorus species that subsequently migrate into the internal alkyne of the 1,3-enynes and protonate the resulting vinyl nickel species, leading to various phosphinoyl 1,3-butadienes under mild reaction conditions.
Visible-light-induced ligand to metal charge transfer excitation enabled phosphorylation of aryl halides
Hou, Hong,Zhou, Bing,Wang, Jiawei,Sun, Duhao,Yu, Huaguang,Chen, Xiaoyun,Han, Ying,Shi, Yaocheng,Yan, Chaoguo,Zhu, Shaoqun
supporting information, p. 5702 - 5705 (2021/06/16)
We herein described a visible light induced nickel(II)-catalyzed cross-coupling of secondary phosphine oxides with aryl halides. The Ni(I)species and chlorine atom radical Cl˙ were generatedviathe ligand to metal charge transfer (LMCT) process of the NiCl2(PPh3)2, which allows nickel(IV)-phosphorus speciesin situformation, giving various tertiary phosphine oxides under photocatalyst-free conditions.
B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids
Jiang, Jun,Zhang, Xinzhi,Zhang, Yangyang,Zhao, Jincheng
supporting information, p. 5772 - 5776 (2021/07/12)
A highly efficient base-, metal-, and oxidant-free catalytic O-H insertion reaction of diazoalkanes and phosphinic acids in the presence of B(C6F5)3has been developed. This powerful methodology provides a green approach towards the synthesis of a broad spectrum of α-phosphoryloxy carbonyl compounds with good to excellent yields (up to 99% yield). The protocol features the advantages of operational simplicity, high atom economy, practicality, easy scalability and environmental friendliness.
Asymmetric synthesis of stereogenic phosphorus P(V) centers using chiral nucleophilic catalysis
Brichacek, Matthew,Numan, Ahmed
, (2021/07/02)
Organophosphates have been widely used in agrochemistry, as reagents for organic synthesis, and in biochemistry. Phosphate mimics possessing four unique substituents, and thereby a chirality center, are useful in transition metal catalysis and as nucleotide therapeutics. The catalytic, stereocontrolled synthesis of phosphorus‐stereogenic centers is challenging and traditionally depends on a resolution or use of stochiometric auxiliaries. Herein, enantioenriched phosphorus centers have been synthesized using chiral nucleophilic catalysis. Racemic H‐phosphinate species were coupled with nucleophilic alcohols under halogenating conditions. Chiral phosphonate products were synthesized in acceptable yields (33–95%) and modest enantioselectivity (up to 62% ee) was observed after identification of an appropriate chiral catalyst and optimization of the solvent, base, and temperature. Nucleophilic catalysis has a tremendous potential to produce enantioenriched phosphate mimics that could be used as prodrugs or chemical biology probes.
Continuous flow esterification of a H-phosphinic acid, and transesterification of H-phosphinates and H-phosphonates under microwave conditions
Henyecz, Réka,Keglevich, Gy?rgy,Kiss, Nóra Zsuzsa
, (2020/02/18)
The microwave (MW)-assisted direct esterification of phenyl-H-phosphinic acid, transesterification of the alkyl phenyl-H-phosphinates so obtained, and the similar reaction of dibenzyl phosphite (DBP) were investigated in detail, and the batch accomplishme
Practical Synthesis of Phosphinic Amides/Phosphoramidates through Catalytic Oxidative Coupling of Amines and P(O)?H Compounds
Tan, Chen,Liu, Xinyuan,Jia, Huanxin,Zhao, Xiaowen,Chen, Jian,Wang, Zhiyong,Tan, Jiajing
supporting information, p. 881 - 887 (2020/01/02)
Herein, we report a highly efficient ZnI2-triggered oxidative cross-coupling reaction of P(O)?H compounds and amines. This operationally simple protocol provides unprecedented generic access to phosphinic amides/phosphoramidate derivatives in good yields and short reaction time. Besides, the reaction proceeds under mild conditions, which avoids the use of hazardous reagents, and is applicable to scale-up syntheses as well as late-stage functionalization of drug molecules. The stereospecific coupling is also achieved from readily available optically enriched P(O)?H compounds.
Transition Metal-Free Synthesis of α-Aminophosphine Oxides through C(sp3)?P Coupling of 2-Azaallyls
Wang, Jing,Deng, Guogang,Liu, Chunxiang,Chen, Zhuo,Yu, Kaili,Chen, Wen,Zhang, Hongbin,Yang, Xiaodong
supporting information, p. 2268 - 2273 (2020/03/04)
Radical reactions have been widely applied in C?P bond-forming strategies. Most of these strategies require initiators, transition metal catalysts, or organometallic reagents. Herein, a transition metal-free C(sp3)?P bond formation to prepare α
Enantiodivergent Synthesis of Both PAMPO Enantiomers Using l -Menthyl Chloroacetate and Stereomutation at P in Classical Quaternisation Reactions
Dziuba, Kamil,Lubańska, Ma?gorzata,Pietrusiewicz, K. Micha?
, p. 909 - 916 (2020/03/13)
A practical protocol for efficient synthesis of both PAMPO enantiomers as well as related functionalised P-stereogenic phosphine oxides in 1-3 steps from effectively resolved (S P)- l -menthyl o -anisyl-(phenyl)phosphinylacetate has been develo
