13238-16-9Relevant academic research and scientific papers
Reactions of elemental phoshorus and phosphine with electrophiles in superbasic systems: XIX. Formation of the C-P bond with participation of elemental phosphorus under microwave assistance
Malysheva,Gusarova,Kuimov,Sukhov,Kudryavtsev,Sinyashin,Budnikova,Pai,Tolstikov,Trofimov
, p. 415 - 420 (2007)
Microwave irradiation facilitates phosphorylation of aryl methyl chlorides and styrene with red phosphorus in the presence of strong bases and increases the yield of the main products, tertiary phosphine oxides. Nauka/Interperiodica 2007.
Reactions of elemental phosphorus and phosphine with electrophiles in superbasic systems: XVI. Phosphorylation of benzyl chloride with elemental phosphorus and phosphine
Trofimov,Gusarova,Malysheva,Shaikhudinova,Belogorlova,Kazantseva,Sukhov,Plotnikova
, p. 684 - 688 (2005)
The major product of the reaction of benzyl chloride with red phosphorus in the system concentrated aqueous KOH-dioxane-phase-transfer catalyst (43-95°C, Ar) is tribenzylphosphine oxide (yield up to 61%). Under similar conditions, phosphorylation of benzy
Highly Enantioselective Synthesis of Phosphorus-Containing ?-Benzosultams by Bifunctional Phosphonium Salt-Promoted Hydrophosphonylation
Zhang, Song,Feng, Zhenghuai,Jiang, Chunhui,Yu, Xiaojun,Pan, Jianke,Du, Juan,Jiang, Zhiyu,Chen, Yuan,Wang, Tianli
, p. 11285 - 11290 (2021)
?-Benzosultam derivatives are potential drug candidates with diverse biological activities. A series of chiral ?-benzosultams bearing phosphorus functionalities was synthesized by catalytic asymmetric hydrophosphonylation in the presence of a bifunctional phosphonium salt catalyst. The desired hydrophosphonylation products were obtained in good yields with high enantioselectivities, and scale-up reactions and further derivations were successfully accomplished. Some control experiments were also conducted to elucidate the plausible reaction mechanism of this chemical transformation.
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.
Siladifluoromethylation and Deoxo-trifluoromethylation of PV-H Compounds with TMSCF3: Route to PV-CF2- Transfer Reagents and P-CF3 Compounds
Krishnamurti, Vinayak,Barrett, Colby,Prakash, G. K. Surya
supporting information, p. 1526 - 1529 (2019/03/07)
A method for siladifluoromethylation of dialkyl phosphonates and secondary phosphine oxides with TMSCF3 to produce nucleophilic PV-CF2- transfer reagents is disclosed, with multigram scale reactions included. Condition-dependent divergent reactivity under the established conditions is demonstrated by the formation of trifluoromethylphosphines. Both one-pot transformations are operationally simple and employ inexpensive materials. Mechanistic investigations suggest the divergent reactivity originates from a common intermediate, with Li+ concentration directing the chemoselectivity.
Electrochemical Dehydrogenative Phosphorylation of Alcohols for the Synthesis of Organophosphinates
Deng, Lingling,Wang, Yang,Mei, Haibo,Pan, Yi,Han, Jianlin
, p. 949 - 956 (2019/01/14)
An eco-friendly and efficient method for the synthesis of organophosphinates via an electrochemical cross-dehydrogenative-coupling reaction between alcohols and secondary phosphine oxides has been developed. This electrochemical reaction was conducted at
Microwave-assisted synthesis of α-aminophosphine oxides
Tripolszky, Anna,Bálint, Erika,Keglevich, Gy?rgy
, p. 345 - 348 (2019/03/07)
Aminophosphine oxides and bis(phosphinoylmethyl)amines were synthesized by the microwave (MW)-assisted Kabachnik-Fields reaction of primary amines, paraformaldehyde and secondary phosphine oxides. The bisphosphines obtained after deoxygenation of the bis(phosphinoymethyl)amine derivatives were utilized in the synthesis of cyclic transition metal complexes.
Selective P?C(sp3) Bond Cleavage and Radical Alkynylation of α-Phosphorus Alcohols by Photoredox Catalysis
Jia, Kunfang,Li, Junzhao,Chen, Yiyun
supporting information, p. 3174 - 3177 (2018/02/09)
Herein the first P?C(sp3) bond cleavage and radical alkynylation of α-phosphorus alcohols to construct phosphonoalkynes is reported. The phosphorus radical is generated upon P?C bond cleavage reaction via the alkoxyl radical through photoredox catalysis with cyclic iodine(III) reagents. Various arylphosphinoyl-, alkylphosphinoyl-, phosphonate-, and phosphonic amide alcohols serve as radical phosphorus precursors to construct phosphonoalkynes for the first time.
Outer-Sphere Reactivity Shift of Secondary Phosphine Oxide-Based Nickel Complexes: From Ethylene Hydrophosphinylation to Oligomerization
Lhermet, Rudy,Moser, Emile,Jeanneau, Erwann,Olivier-Bourbigou, Hélène,Breuil, Pierre-Alain R.
supporting information, p. 7433 - 7437 (2017/06/06)
A new dimension for secondary phosphine oxide (SPOs) ligands is described in this article. Demonstrated on original π-allylic nickel structures, these self-assembled complexes trigger catalytic hydrophosphinylation reactions. Addition of a Lewis acid B(C6F5)3 switches the reactivity towards migratory insertion and thus ethylene oligomerization through an unprecedented outer-sphere interaction with the coordinated SPO ligand. NMR experiments and X-ray analyses allowed for the observation of the formation of zwitterionic active species as well as their degradation pathway.
Synthesis and use of α-aminophosphine oxides and N,N-bis(phosphinoylmethyl)amines - A study on the related ring platinum complexes
Bálint, Erika,Tripolszky, Anna,Jablonkai, Erzsébet,Karaghiosoff, Konstantin,Czugler, Mátyás,Mucsi, Zoltán,Kollár, László,Pongrácz, Péter,Keglevich, Gy?rgy
, p. 111 - 121 (2015/11/24)
The Kabachnik-Fields condensation was extended using secondary phosphine oxides, such as dibenzylphosphine oxide and bis(4-methylphenyl)phosphine oxide as the P-reactant in reaction with formaldehyde and different primary amines. Besides the α-aminophosphine oxides, the corresponding bisproducts, N,N-bis(phosphinoylmethyl)amines were also synthesized under appropriate conditions. The bis(phosphinoyl)amines were then converted to ring platinum complexes after double deoxygenation. The substituent dependence of the energetics of the complexation reaction using bidentate P-ligands, and the stereostructure of a few complexes were evaluated by B3LYP/6-31G(d,p) calculations using the effective core potential (ECP) basis set (SDD). The crystal structure of a few ring Pt species was studied by X-ray analysis. Catalytic activity of the complexes synthesized was investigated in hydroformylation.
