P-Chiral Phosphines Enabled by Palladium/Xiao-Phos-Catalyzed Asymmetric P–C Cross-Coupling of Secondary Phosphine Oxides and Aryl Bromides

2019 ◽  
Vol 141 (51) ◽  
pp. 20556-20564 ◽  
Author(s):  
Qiang Dai ◽  
Wenbo Li ◽  
Zhiming Li ◽  
Junliang Zhang
Keyword(s):  
Cross Coupling ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Aryl Bromides ◽  
Chiral Phosphines

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

scholarly journals Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides

2010 ◽  
Vol 51 (42) ◽  
pp. 5550-5554 ◽  
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

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.

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.

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