Zirconium-catalyzed intermolecular hydrophosphination using a chiral, air-stable primary phosphine

2016 ◽  
Vol 45 (5) ◽  
pp. 1863-1867 ◽  
Author(s):  
Christine A. Bange ◽  
Michael B. Ghebreab ◽  
Arne Ficks ◽  
Neil T. Mucha ◽  
Lee Higham ◽  
...  
Keyword(s):  
Slight Modification ◽  
Secondary Phosphine ◽  
Tertiary Phosphine ◽  
Mild Conditions ◽  
Primary Phosphine

Catalytic hydrophosphination of alkenes using a chiral, air-stable primary phosphine, (R)-MeO-MOPH2, proceeds under mild conditions with a zirconium catalyst to selectively furnish anti-Markovnikov, air-stable secondary phosphine or tertiary phosphine prodcuts with slight modification of the protocol.

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

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.

Novel Class of Tertiary Phosphine Ligands Based on a Phospha-adamantane Framework and Use in the Suzuki Cross-Coupling Reactions of Aryl Halides under Mild Conditions

2003 ◽  
Vol 5 (6) ◽  
pp. 953-955 ◽  
Author(s):  
George Adjabeng ◽  
Tim Brenstrum ◽  
Jeffrey Wilson ◽  
Christopher Frampton ◽  
Al Robertson ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Phosphine Ligands ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Tertiary Phosphine ◽  
Mild Conditions ◽  
Cross Coupling Reactions

ChemInform Abstract: Facile Non-Catalyzed Synthesis of Tertiary Phosphine Sulfides by Regioselective Addition of Secondary Phosphine Sulfides to Alkenes.

ChemInform ◽  
2015 ◽  
Vol 46 (6) ◽  
pp. no-no
Author(s):  
Svetlana F. Malysheva ◽  
Nina K. Gusarova ◽  
Alexander V. Artem'ev ◽  
Nataliya A. Belogorlova ◽  
Alexander I. Albanov ◽  
...  
Keyword(s):  
Secondary Phosphine ◽  
Tertiary Phosphine ◽  
Regioselective Addition

Metal-free site selective cross-coupling of pyridines with secondary phosphine chalcogenides using acylacetylenes as oxidants

2018 ◽  
Vol 54 (27) ◽  
pp. 3371-3374 ◽  
Author(s):  
Boris A. Trofimov ◽  
Pavel A. Volkov ◽  
Kseniya O. Khrapova ◽  
Anton A. Telezhkin ◽  
Nina I. Ivanova ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Secondary Phosphine ◽  
Metal Free ◽  
Mild Conditions ◽  
Secondary Phosphine Chalcogenides ◽  
Site Selective ◽  
Phosphine Chalcogenides

Pyridines are easily cross-coupled with secondary phosphine chalcogenides in the presence of acylphenylacetylenes under mild conditions to afford 4-chalcogenophosphorylpyridines.

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.

Catalyst- and Solvent-Free Rapid Addition of Secondary Phosphine Chalcogenides to Aldehydes: Another Click Chemistry

Synthesis ◽  
2015 ◽  
Vol 47 (11) ◽  
pp. 1611-1622 ◽  
Author(s):  
Nina Gusarova ◽  
Nina Ivanova ◽  
Pavel Volkov ◽  
Kseniya Khrapova ◽  
Luydmila Larina ◽  
...  
Keyword(s):  
Click Chemistry ◽  
Solvent Free ◽  
Secondary Phosphine ◽  
Efficient Catalyst ◽  
Mild Conditions ◽  
Secondary Phosphine Chalcogenides ◽  
Phosphine Chalcogenides

An efficient catalyst- and solvent-free method for the synthesis of tertiary α-hydroxyphosphine chalcogenides, via the almost quantitative addition of secondary phosphine chalcogenides to diverse aldehydes under mild conditions (20–52 °C, from 10 min to 5 h), is reported.

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