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.

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.

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

Organophosphorverbindungen mit tertiären Alkylsubstituenten. III*: Synthese und Reaktionen Di-1-adamantylsubstituierter Phosphorverbindungen; Kristallstruktur von Di-1-Adamantylphosphinsäurechlorid / Organophosphorus Compounds with Tertiary Alkyl Substituents. Ill: Synthesis and Reactions of Di-1-adam antyl-Substituted Phosphorus Compounds; Crystal Structure of Di-1-adam antylphosphinic Chloride

1994 ◽  
Vol 49 (6) ◽  
pp. 801-811 ◽  
Author(s):  
Jens R. Goerlich ◽  
Axel Fischer ◽  
Peter G. Jones ◽  
Reinhard Schmutzler
Keyword(s):  
Organophosphorus Compounds ◽  
Phosphorus Compounds ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
X Ray ◽  
Dry Air ◽  
Nmr Data ◽  
Standard Procedures ◽  
Hydrolysis Of ◽  
Tertiary Alkyl

The reaction of adamantane with PCl3/A1Cl3, followed by hydrolysis, gave (1-Ad)2P(:O)Cl 1, which was converted to (1-Ad)2P(:O)F 2 and (1-Ad)2P(:S)Cl 3 by standard procedures. The structure of 1 was confirmed by a single crystal X-ray structure determination; despite the bulky substituents the P-C bond lengths are normal (184.0(3), 185.0(3) pm). Whereas chlorine-fluorine exchange in 3 with AsF3 furnished (1-Ad)2P(:S)F 4, desulfuration of 3 with Ph3P to give (1-Ad)2PCl 5 failed. The secondary phosphine oxides R 1R2P(:O)H (R1, R2 = 1-Ad: 6; R1 = 1-Ad, R2 = tBu: 7; R1, R2 = tBu: 8) were synthesized by reaction of 1, 1-AdP(:O)Cl2 and tBuP(:0)Cl2 with tBuLi. 6 and 8 reacted readily with chloral to give the adducts R2P(:O)CH(OH)CCl3 (R = 1-Ad: 9; R = tBu: 10). Silylation of 6 with Me2NSiMe3 in the presence of dry air led to (1-Ad)2P(:O)OSiMe3 11, which was hydrolyzed to give (1-Ad)2P(:O)OH 12. (1-Ad)2POSiMe3 13 was obtained by the reaction of 6 with n-BuLi, followed by Me3SiCl. No reaction took place upon heating 6 with Mo(CO)6. (1-Ad)2PCl 5 was synthesized in low yield by the reaction of 6 with PCl3. The action of tetrachloro-obenzoquinone (TOB) upon 6 furnished (1-Ad)2P(:O)(o-OH)C6Cl4 15, whereas the tbutyl analogue of 15, 16, was synthesized by hydrolysis of the TOB-adduct of di-tbutylfluorophosphine. Analogous 1-adamantyl- and tbutyl-phosphorus compounds are compared with regard to their 31P NMR data

Palladium-catalyzed dehydrogenative coupling of terminal alkynes with secondary phosphine oxides

2015 ◽  
Vol 51 (17) ◽  
pp. 3549-3551 ◽  
Author(s):  
Jia Yang ◽  
Tieqiao Chen ◽  
Yongbo Zhou ◽  
Shuangfeng Yin ◽  
Li-Biao Han
Keyword(s):  
Reaction Mechanism ◽  
Palladium Acetate ◽  
Secondary Phosphine ◽  
Terminal Alkynes ◽  
Phosphine Oxides ◽  
Dehydrogenative Coupling ◽  
Palladium Catalyzed ◽  
High Yields

The palladium-catalyzed dehydrogenative coupling of alkynes with secondary phosphine oxides is developed. Thus, in the presence of a silver additive, palladium acetate could efficiently catalyze the dehydrocoupling of secondary phosphine oxides with a variety of alkynes to produce the corresponding alkynylphosphine oxides in high yields. A reaction mechanism is proposed.

ChemInform Abstract: Rapid Synthesis of an Electron-Deficient t-BuPHOX Ligand: Cross-Coupling of Aryl Bromides with Secondary Phosphine Oxides.

ChemInform ◽  
2011 ◽  
Vol 42 (5) ◽  
pp. no-no
Author(s):  
Nolan T. McDougal ◽  
Jan Streuff ◽  
Herschel Mukherjee ◽  
Scott C. Virgil ◽  
Brian M. Stoltz
Keyword(s):  
Cross Coupling ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Rapid Synthesis ◽  
Aryl Bromides
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