Copper‐Catalyzed C‐P Cross‐Coupling of (Cyclo)alkenyl/Aryl Bromides and Secondary Phosphine Oxides with in situ Halogen Exchange

2021 ◽  
Author(s):  
Paweł Woźnicki ◽  
Marek Stankevič
Keyword(s):  
Cross Coupling ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Aryl Bromides ◽  
Halogen Exchange

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

scholarly journals Air and water stable secondary phosphine oxides as diazaphospholene precatalysts

2020 ◽  
Vol 56 (58) ◽  
pp. 8027-8030 ◽  
Author(s):  
Travis Lundrigan ◽  
Chieh-Hung Tien ◽  
Katherine N. Robertson ◽  
Alexander W. H. Speed
Keyword(s):  
Secondary Phosphine ◽  
Phosphine Oxides

Secondary phosphine oxides, which are air and water stable, and purifiable by chromatography generate phosphenium or phosphorus hydride catalysts in situ.

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.

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