α-Phosphino Amino Acids: Synthesis, Structure, and Reactivity

Heinicke, Joachim; Lach, Joanna; Basvani, Kaleswara R.; Peulecke, Normen; Jones, Peter G.; Köckerling, Martin

doi:10.1080/10426507.2010.514485

Cited by 16 publications

(4 citation statements)

References 59 publications

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“…We describe herein for the first time the formation of aminophosphonoacetic acids through the reaction of glyoxylic acid with a mixture of amine and phosphorous acid. The Kabachnik-Fields reaction of phosphines was reported by J. Heinicke et al [27,28] but the Moedritzer-Irani reaction with glyoxylic acid was not reported.…”

Section: Resultsmentioning

confidence: 98%

MCR under Microwave Irradiation: Synthesis in Water of New 2-Amino-bis(2-phosphonoacetic) Acids

2021

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Novel 2-amino bis(2-phosphonoacetic) acids were prepared by microwave irradiation of a mixture of amine, glyoxylic acid and phosphorous acid. The reaction takes place with various amines including primary and secondary amines and polyamines, but this reaction is more sensitive to steric hindrance of amine than the similar Kabachnik–Fields reaction. Amino acids can be also transformed into the expected bis(2-phosphonoacetic) acids, with the exception of tryptophan, which gives a β-carboline product.

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Section: Resultsmentioning

confidence: 98%

MCR under Microwave Irradiation: Synthesis in Water of New 2-Amino-bis(2-phosphonoacetic) Acids

2021

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“…In comparison to nickel catalysts based on N-substituted diphenylphosphinoglycine or 3-phenyl-1,3-azaphospholidine-2-carboxylic acid, the efficiency of 12a , b /Ni for ethylene conversion is improved. Therefore, and because incorporation of styrene comonomers into the CH 2 chain was observed for o -phosphinophenolate nickel catalysts, we tested if copolymerization of ethylene with styrene is possible.…”

Section: Resultsmentioning

confidence: 99%

Enantiomerically Pure N Chirally Substituted 1,3-Benzazaphospholes: Synthesis, Reactivity toward tBuLi, and Conversion to Functionalized Benzazaphospholes and Catalytically Useful Dihydrobenzazaphospholes

et al. 2014

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Catalytic C−P coupling of chiral o-bromoanilines 1a−c to the corresponding o-phosphonoanilines 2a−c, reduction to the phosphines 3a−c, and final acid-catalyzed cyclocondensation represents a convenient access to the title compounds 4a−c. Reaction of 4a,b with tBuLi allows solventdependent directed lithiation leading either to 2-lithiobenzazaphospholes with a −PCLi−NR− substructure (in Et 2 O/ KOtBu), in the case of anisyl substitution accompanied by partial additional lithiation in o-position of the MeO-group, or to regiospecific "normal" addition with formation of −P-(tBu)−CHLi−NR− species. These were trapped by ClSiMe 3 , CO 2 , or MeOH to give the corresponding substitution products 7b, 8b, 10b, 11a,b and 12a,b, respectively. 12a,b, containing the P−C−COOH structural unit, forms with Ni(COD) 2 in THF very efficient ethylene oligomerization catalysts with high selectivity for linear α-olefins. The structure elucidation of the products is based on conclusive solution NMR data and crystal structure analyses of the 1-(1S)-anisylethyl compounds 3b and 4b.

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“…Tests of 31a in the Pd‐catalyzed C–N cross‐coupling of mesityl bromide with 2‐bromopyridine and of the heterocyclic phosphanylaminoacetic acids 31 – 33b in the Ni‐catalyzed ethylene oligomerization showed formation of moderately and highly active catalysts, respectively 35b,72. Tests with less bulky N‐ or P ‐substituted benzazaphospholine‐2‐carboxylate Ni catalysts gave rise to lower activity in the latter reaction and suggest that sterically more demanding N‐substituents prevent interfering interactions of nitrogen with the catalyst metal 75–77…”

Section: Recent Syntheses and New Types Of Electron‐rich Heterophomentioning

confidence: 99%

Electron‐Rich Aromatic 1,3‐Heterophospholes – Recent Syntheses and Impact of High Electron Density at σ²P on the Reactivity

Heinicke

2015

Eur J Inorg Chem

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This account reviews recent syntheses, properties, and the reactivity of electron‐rich aromatic 1,3‐heterophospholes, with the focus on benzazaphospholes, but also with inclusion of 1,2,4‐diazaphospholes containing the N–C=P–C motif and related O‐ and S‐containing heterocycles. Effects of the high electron density at phosphorus, a consequence of the position of the lone‐pair donating nitrogen atom in conjugation with dicoordinated (σ2) phosphorus and of the absence of P–N bonds, are illuminated by comparison of selected properties and reactions with those of less electron‐rich heterophospholes and phosphinines. Particular features of the electron‐rich heterocycles are CH‐lithiations of the P=CH fragment by tBuLi without addition at the P=C double bond in polar media, occurrence of inverse addition besides normal addition in less polar solutions, P‐alkylation and catalytic P‐arylation, and – last but not least – the avoidance of σ‐coordination of non‐zerovalent d10 transition metals within the ring plane in favor of μ2‐P and/or tilted η1‐P coordination.

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α-Phosphino Amino Acids: Synthesis, Structure, and Reactivity

Cited by 16 publications

References 59 publications

MCR under Microwave Irradiation: Synthesis in Water of New 2-Amino-bis(2-phosphonoacetic) Acids

MCR under Microwave Irradiation: Synthesis in Water of New 2-Amino-bis(2-phosphonoacetic) Acids

Enantiomerically Pure N Chirally Substituted 1,3-Benzazaphospholes: Synthesis, Reactivity toward tBuLi, and Conversion to Functionalized Benzazaphospholes and Catalytically Useful Dihydrobenzazaphospholes

Electron‐Rich Aromatic 1,3‐Heterophospholes – Recent Syntheses and Impact of High Electron Density at σ²P on the Reactivity

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α-Phosphino Amino Acids: Synthesis, Structure, and Reactivity

Cited by 16 publications

References 59 publications

MCR under Microwave Irradiation: Synthesis in Water of New 2-Amino-bis(2-phosphonoacetic) Acids

MCR under Microwave Irradiation: Synthesis in Water of New 2-Amino-bis(2-phosphonoacetic) Acids

Enantiomerically Pure N Chirally Substituted 1,3-Benzazaphospholes: Synthesis, Reactivity toward tBuLi, and Conversion to Functionalized Benzazaphospholes and Catalytically Useful Dihydrobenzazaphospholes

Electron‐Rich Aromatic 1,3‐Heterophospholes – Recent Syntheses and Impact of High Electron Density at σ2P on the Reactivity

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Electron‐Rich Aromatic 1,3‐Heterophospholes – Recent Syntheses and Impact of High Electron Density at σ²P on the Reactivity