Methyl(cyanomethyl)phosphines. Synthesis and Nucleophilic Reactivity.

Dahl, Otto; Henriksen, Ulla; Trebbien, Claus; Carlberg, Georg E.; Sterner, Olov; Wickberg, Börje

doi:10.3891/acta.chem.scand.37b-0639

Cited by 7 publications

(3 citation statements)

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“…The latter compound was (without isolation) oxidised with PhIO 2 to give the desired phosphine oxide 2 in 40% yield after purification (Scheme 2). Alternative methods for the synthesis of 2, as previously described by Dahl et al, 13,14 appeared to be unsuccessful in our hands.…”

Section: Resultsmentioning

confidence: 83%

Enzyme-promoted desymmetrisation of prochiral bis(cyanomethyl)phenylphosphine oxide

Kiełbasiński

Rachwalski

Kwiatkowska

et al. 2007

Tetrahedron: Asymmetry

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Section: Resultsmentioning

confidence: 83%

Enzyme-promoted desymmetrisation of prochiral bis(cyanomethyl)phenylphosphine oxide

Kiełbasiński

Rachwalski

Kwiatkowska

et al. 2007

Tetrahedron: Asymmetry

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“…The synthetic route to bis-and tris(cyanomethyl) phosphines was developed based on the application of Reformatskii reagent (Scheme 18) [41].…”

Section: Alkylation Of Metal Phosphides and Phosphorylation Of Organomentioning

confidence: 99%

Synthesis and Coordination Chemistry of Cyano-Substituted Phosphines

Odinets¹,

Vinogradova²,

Matveeva³

et al. 2005

COC

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Synthetic approaches to both linear and cyclic cyano-substituted phosphines (P~CN-phosphines) found an industrial application as catalyst precursors, pesticides, herbicides, flame retardants, precursors of aminophosphines etc., are reported. The main synthetic routes include reduction of P=O containing precursors, alkylation of silylphosphines and metal phosphides by halogenoalkyl(aryl)carbonitriles, phosphorylation of the latter ones, decomposition of phosphonium salts and hydrophosphination of cyano-substituted olefins proceeding under non-catalytical conditions and with use of metal complex catalysis. Merits and demerits of each approach are discussed. Phosphines bearing cyano function as an additional coordination site show diverse coordination behavior depending on the phosphine structure and nature of the metal. Four main types of complexes are observed, namely those with P-monodentate coordination, with N-monodentate coordination and complexes where bidentate coordination mode of P and N atoms is realized either at the single metal atom or of bridged type between two different metal atoms. Thus coordination behavior of such P~CN-ligands relative to transition and non-transition metals, structure features of the complexes obtained and their application in catalytic processes are discussed.

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“…The favored reaction in Scheme should have several advantages, such as the decreased tendency of multiple substitutions and a large toleration of functional groups. In fact, organozinc compounds have been widely used before for the formation of P–C bonds, e.g., in the synthesis of organophosphonates and tertiary phosphines like (cyanomethyl)phosphines with two or three cyanomethyl groups, polyfunctional phosphines, or chiral phosphines. − …”

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confidence: 99%

The Formation of P–C Bonds Utilizing Organozinc Reagents for the Synthesis of Aryl- and Heteroaryl-Dichlorophosphines

et al. 2021

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Aryl- and heteroaryl-dichlorophosphines are mildly and selectively made in a one-pot synthesis in moderate to good yields starting from the respective aryl bromides or five-membered heterocycles, following lithiation with nBuLi, transmetalation with ZnCl2, and subsequently the reaction with PCl3. Selected aryl- and heteroaryl-dichlorophosphines were successfully synthesized using this reaction method and could easily be purified after isolation. The intermediate formation of the organozinc species is essential, as it prevents the formation of multiple substitution products. Important are also the reaction conditions: the usage of the proper solvent for the respective aromatic precursors and removal of the remaining salts by addition of a dioxane/pentane mixture. Depending on the solvent and steric demand of the substituent, mono- and bis-substitution products can be formed but formation also prevented. Hereby, different organozinc species might play an important role.

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Methyl(cyanomethyl)phosphines. Synthesis and Nucleophilic Reactivity.

Cited by 7 publications

References 0 publications

Enzyme-promoted desymmetrisation of prochiral bis(cyanomethyl)phenylphosphine oxide

Enzyme-promoted desymmetrisation of prochiral bis(cyanomethyl)phenylphosphine oxide

Synthesis and Coordination Chemistry of Cyano-Substituted Phosphines

The Formation of P–C Bonds Utilizing Organozinc Reagents for the Synthesis of Aryl- and Heteroaryl-Dichlorophosphines

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