The Primary Phosphine Renaissance

Higham, Lee J.

doi:10.1007/978-90-481-3817-3_1

Cited by 8 publications

(3 citation statements)

References 79 publications

(65 reference statements)

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“…Further, we decided to generate the phosphine radical of phenyl phosphine electrochemically. During CV measurements, we observed irreversible oxidation to the radical cation as known from the literature [5a] . Unfortunately, the addition of decamethyl‐ferrocene to the solution did not lead to a reversible electrochemical pathway or quenching of the generated cation, under our experimental conditions.…”

Section: Resultssupporting

confidence: 70%

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A General Strategy for Increasing the Air Stability of Phosphines Including Primary Phosphines

Horký,

Franz,

Bruhn

et al. 2023

Chemistry A European J

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Given recent reports of structurally diverse air‐stable primary phosphines lacking kinetic stabilization, the stability against oxidation was difficult to rationalize and attributed to the specific electronic nature of the phosphine group. This contribution shows the synthesis of a series of air‐stable primary phosphines Fc(CH2)nPH2, where n = 0,1,2,3; and Fc = ferrocenyl, and their corresponding isolable primary phosphine oxides. It was demonstrated that the ferrocene moiety exerts an antioxidant effect on the primary phosphine group, which is intermolecular, solvent dependent and increases with the electron density on the ferrocene moiety. Furthermore, we demonstrated that the presence of ferrocene in solution also inhibits the oxidation of other secondary and tertiary phosphines in air. The collected information suggests that quenching of singlet oxygen is the actual reason for the antioxidant effect which was experimentally confirmed using other established singlet oxygen quenchers as well, demonstrating a key role of singlet oxygen in the aerobic oxidation of phosphines.

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Section: Resultssupporting

confidence: 70%

“…Despite what was mentioned before, there is an exciting group of air‐stable primary phosphines where steric hindrance cannot be the protecting factor (Scheme 1E) [5a,b,8] . Their stability is challenging to be rationalized.…”

Section: Introductionmentioning

confidence: 99%

A General Strategy for Increasing the Air Stability of Phosphines Including Primary Phosphines

Horký,

Franz,

Bruhn

et al. 2023

Chemistry A European J

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“…However, recent developments in fundamental phosphorus chemistry have identified a systematic way to classify specific primary phosphines as air-stable that possess remarkable oxidative resistance not explained simply by substituent steric effects . This has initiated what some refer to as “The Primary Phosphine Renaissance” …”

Section: Introductionmentioning

confidence: 99%

Polymer Network Formation Using the Phosphane–ene Reaction: A Thiol–ene Analogue with Diverse Postpolymerization Chemistry

et al. 2015

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Air-stable primary phosphines were photopolymerized using phosphane−ene chemistry, the phosphorus analogue of the thiol−ene reaction, to fabricate a completely new class of polymer networks. It was demonstrated that the tunable thermal and physical properties accessible using thiol−ene chemistry could also be achieved using an analogous phosphane−ene reaction. At the same time, the presence of the 31 P nucleus that is easily observed using NMR spectroscopy allowed the chemical structures of the networks to be directly probed using solid state NMR spectroscopy. Following its incorporation into the network, phosphorus offers the distinct difference and advantage of being able to undergo a diverse array of further derivatization to afford functional materials. For example, the networks were demonstrated to serve as effective oxygen scavengers and to bind transition metals (e.g., Pd). By using the air stable ferrocenyl phosphine (FcCH 2 CH 2 )PH 2 , redoxactive networks were produced and these materials could be pyrolyzed to yield magnetic ceramics. Overall, this demonstrates the promise of phosphane−ene chemistry as an alternative to thiol−ene systems for providing functional materials for a diverse range of applications.

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Synthesis of P‐Arylphosphinecarboxamide Derivatives by Addition of N‐Arylphosphinecarboxamides with Aryne Precursors

Wang

Cui

et al. 2022

Asian J Org Chem

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A reliable method for preparing P(III)‐arylphosphinecarboxamide derivatives from N‐arylphosphinecarboxamides and aryne precursors has been developed. This reaction was carried out without transition‐metal catalysts, and a series of unsymmetrically structured phosphinecarboxamide derivatives were obtained under mild conditions. In addition, the reaction is carried out under air atomosphere, and the corresponding P(III)‐aryl phosphinecarboxamide compounds are also stable in air.

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The Primary Phosphine Renaissance

Cited by 8 publications

References 79 publications

A General Strategy for Increasing the Air Stability of Phosphines Including Primary Phosphines

A General Strategy for Increasing the Air Stability of Phosphines Including Primary Phosphines

Polymer Network Formation Using the Phosphane–ene Reaction: A Thiol–ene Analogue with Diverse Postpolymerization Chemistry

Synthesis of P‐Arylphosphinecarboxamide Derivatives by Addition of N‐Arylphosphinecarboxamides with Aryne Precursors

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