Developing five-membered heterocycle substituted phosphinous acids as ligands for palladium-catalyzed Suzuki–Miyaura and Catellani reactions

2015 ◽  
Vol 44 (39) ◽  
pp. 17129-17142 ◽  
Author(s):  
Ting-Wei Chang ◽  
Pei-Yun Ho ◽  
Kuo-Chung Mao ◽  
Fung-E. Hong
Keyword(s):  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Organic Products ◽  
Palladium Catalyzed ◽  
Membered Heterocycle

Several secondary phosphine oxides (SPOs) were prepared. Organic products with unexpected conformations (9 and 10) were obtained besides 8 from Heck-type Catellani reactions with the assistance of the selected SPO ligand 5f.

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.

scholarly journals Secondary Phosphine Oxides as Multitalented Preligands En Route to the Chemoselective Palladium-Catalyzed Oxidation of Alcohols

ChemCatChem ◽  
2017 ◽  
Vol 9 (5) ◽  
pp. 728-732 ◽  
Author(s):  
Alexandre Vasseur ◽  
Romain Membrat ◽  
David Gatineau ◽  
Alphonse Tenaglia ◽  
Didier Nuel ◽  
...  
Keyword(s):  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Oxidation Of Alcohols ◽  
Palladium Catalyzed ◽  
Catalyzed Oxidation

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.

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

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
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