Preparation of Optically Pure Tertiary Phosphine Oxides via the Addition ofP-Stereogenic Secondary Phosphine Oxide to Activated Alkenes

2016 ◽  
Vol 81 (17) ◽  
pp. 7644-7653 ◽  
Author(s):  
Ji-Ping Wang ◽  
Shao-Zhen Nie ◽  
Zhong-Yang Zhou ◽  
Jing-Jing Ye ◽  
Jing-Hong Wen ◽  
...  
Keyword(s):  
Phosphine Oxide ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Tertiary Phosphine ◽  
Optically Pure

Thermal stability of primary and secondary phosphine oxides formed as a reaction of phosphine oxide with ketones

2016 ◽  
Vol 191 (11-12) ◽  
pp. 1480-1481 ◽  
Author(s):  
E. V. Gorbachuk ◽  
E. K. Badeeva ◽  
S. A. Katsyuba ◽  
P. O. Pavlov ◽  
Kh. R. Khayarov ◽  
...  
Keyword(s):  
Thermal Stability ◽  
Phosphine Oxide ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Thermal Stability Of

Palladium-Catalyzed C–P Cross-Coupling between (Het)aryl Halides and Secondary Phosphine Oxides

Synthesis ◽  
2019 ◽  
Vol 51 (11) ◽  
pp. 2379-2386 ◽  
Author(s):  
Gladis Zakirova ◽  
Dmitrii Mladentsev ◽  
Nataliya Borisova
Keyword(s):  
Electronic Properties ◽  
Heterocyclic Compounds ◽  
Cross Coupling ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Tertiary Phosphine ◽  
Reaction Conditions ◽  
Efficient Procedure ◽  
Palladium Catalyzed ◽  
Tertiary Alkyl

An efficient procedure for C–P bond formation via the palladium-catalyzed [Pd(OAc)2/dppf/Cs2CO3] reaction between dichloroheterocycles and secondary phosphine oxides was developed. The steric and electronic properties of substituents were varied to establish the scope and limitations of the method developed. By applying these conditions, a variety of new heterocyclic compounds bearing two tertiary phosphine oxides were successfully synthesized in moderate to excellent yields. After adjustments to the reaction conditions [Pd(OAc)2/dippf/t-BuOK], cross-coupling of secondary phosphine oxides with bulky (secondary or tertiary alkyl) substituents on the phosphorus atom was achieved. Extension of the methodology to monohalohetarenes and monohaloarenes was successfully carried out; once again, the steric and electronic properties of the halides were varied widely. The desired reaction occurred in all cases studied, giving high to excellent yields of product regardless of the nature and positions of substituents.

Reduction of secondary and tertiary phosphine oxides to phosphines

2015 ◽  
Vol 44 (8) ◽  
pp. 2508-2528 ◽  
Author(s):  
Damien Hérault ◽  
Duc Hanh Nguyen ◽  
Didier Nuel ◽  
Gérard Buono
Keyword(s):  
Phosphine Oxide ◽  
Phosphine Oxides ◽  
Oxide Reduction ◽  
Tertiary Phosphine

In this review, we summarise all the methods of phosphine oxide reduction and discuss their mechanistic aspects.

An Approach to Nonsymmetric Bis(tertiary phosphine oxides) Comprising Heterocyclic Fragments via the Pd-Catalyzed Phosphorylation

Synlett ◽  
2020 ◽  
Vol 31 (18) ◽  
pp. 1833-1837
Author(s):  
Gladis G. Zakirova ◽  
Dmitrii Yu. Mladentsev ◽  
Nataliya N. Borisova
Keyword(s):  
Phosphine Oxide ◽  
Phosphine Ligand ◽  
Nonpolar Solvent ◽  
Phosphine Oxides ◽  
Purification Step ◽  
Tertiary Phosphine ◽  
Phosphorylation Reaction ◽  
Double Coupling

Nonsymmetric tertiary phosphine oxides with different five- and six-membered heterocyclic fragments such as pyridine, 2,2′-bipyridine, 1,10-phenantroline, quinoline, imidazole, and thiazole were synthesized in good yields via the successive introduction of phosphine oxide groups into the initial dihalogenated heterocycles by means of Pd-catalyzed phosphorylation reaction. The synthesis of pyridine-type compounds is hindered by competing double coupling, while for five-membered heterocycles the principal difficulty is the dehalogenation. Both side processes were successfully suppressed by the use of an excess of a dihalide (which can be easily recovered during the product purification step), proper phosphine ligand for palladium, and nonpolar solvent such as toluene.

Secondary phosphine oxide-triggered selective oxygenation of a benzyl ligand on palladium

2020 ◽  
Vol 56 (85) ◽  
pp. 12977-12980
Author(s):  
Sayaka Oka ◽  
Yuma Shigehiro ◽  
Yasutaka Kataoka ◽  
Yasuyuki Ura
Keyword(s):  
Phosphine Oxide ◽  
Secondary Phosphine ◽  
Phosphine Oxides

The oxygenation of a benzyl ligand on palladium was dramatically accelerated by using secondary phosphine oxides, selectively affording BnOOH or BnOH.

scholarly journals Nickel-catalyzed C–P cross-coupling of (het)aryl tosylates with secondary phosphine oxides

2021 ◽  
pp. 174751982199453
Author(s):  
Xiao-Yun He
Keyword(s):  
Cross Coupling ◽  
Phosphorus Compounds ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Tertiary Phosphine ◽  
Convenient Approach ◽  
Aryl Tosylates ◽  
High Yields

A novel and convenient approach to the synthesis of various tertiary phosphine oxides via nickel-catalyzed cross-coupling of (het)aromatic tosylates with secondary phosphine oxides is developed. The reaction employs cheap nickel as the catalyst, 1-(2-(di-tert-butylphosphanyl)phenyl)-4-methoxypiperidine (L3) as the ligand, and pyridine as the base. This reaction produces the corresponding (het)aromatic phosphorus compounds in good to high yields. Moreover, four new tertiary phosphine oxides are reported in this process.

Enantioselective hydrogenation of ketones by iridium nanoparticles ligated with chiral secondary phosphine oxides

2016 ◽  
Vol 6 (11) ◽  
pp. 3758-3766 ◽  
Author(s):  
Israel Cano ◽  
Mathieu J.-L. Tschan ◽  
Luis M. Martínez-Prieto ◽  
Karine Philippot ◽  
Bruno Chaudret ◽  
...  
Keyword(s):  
Phosphine Oxide ◽  
Enantioselective Hydrogenation ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Iridium Nanoparticles

Chiral iridium nanoparticles (IrNPs) were synthesized by H2reduction of (1,5-cyclooctadiene)(methoxy)iridium(i) dimer ([Ir(OMe)(COD)]2) in the presence of an asymmetric secondary phosphine oxide.

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