Phospha-Mannich reactions of phosphinous acids R
            <sub>2</sub>
            P–OH and their derivatives

Moiseev, D. V.

doi:10.1080/10426507.2023.2235054

Cited by 6 publications

(2 citation statements)

References 571 publications

(260 reference statements)

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“…Hexane was layered from a gas phase on the clear yellow solution. After 1 week, a mixture of yellow (6) and colorless (pyridinium chloride) crystals was formed, which were identified by SCXRD. Pyridinium chloride was identified by unit cell parameters (P − 1): a = 4.72 Å, b = 7.49 Å, c = 8.14 Å, α = 87.3°, β = 88.3°, γ = 87.5°, V = 287 Å 3 The mixture was stirred for 1 day at ambient temperature.…”

Section: Methodsmentioning

confidence: 99%

“…Electronic and steric characteristics of phosphines can be readily modified by their functionalization at various positions. Among them, aminophosphines stand out, which contain fundamentally different N and P donor groups. − A wide range of substituents at the heteroatoms, as well as the ability to act as polydentate ligands for different transition metals, allow one to design aminophosphines for many practical applications: biomolecular chemistry, as antitumor agents, activators of small molecules, , and homogeneous , and enantioselective catalysts . Complexes with α-aminophosphines are effective catalysts in reactions of hydroformylation of styrene, , Heck reactions between olefine and aryl halides, , and Suzuki-Miyaura and decarboxylative C–C couplings .…”

Section: Introductionmentioning

confidence: 99%

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Pd(II)- and Pt(II)-Assisted P–C Activation/Cyclization Reactions with a Luminescent α-Aminophosphine

Afonin,

Martynenko,

Kolybalov

et al. 2023

Inorg. Chem.

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There is unceasing interest toward transformations of phosphine derivatives, which are facilitated by transition metals. We report a facile Pd(II)-and Pt(II)-assisted P−C bond cleavage in a luminescent 2-phenylbenzothiazole-based αmethylaminophosphine (PCN, 1). Specifically, reactions between 1 and [M(COD)Cl 2 ] (M = Pd, Pt; COD = cycloocta-1,5-diene) in different solvents (methylene chloride, acetonitrile, pyridine, toluene) resulted in the formation of PPh 2 − , captured either as a bridging ligand in binuclear complexes with a {M 2 (PPh 2 ) 2 } moiety or as an adduct to COD in [Pt 2 (PPh 2 COD) 2 Cl 2 ]. The heterocyclic part transforms to annulated c-CN + species with a 1,2-dihydroquinazoline cycle formed. In the presence of pyridine as a base, annulated form c-CN + destabilizes and undergoes reverse cyclization transforming to deprotonated CN form. Quantum-chemical density functional theory (DFT) calculations predict that a crucial step in the reactions involves proton transfer from the N atom of the amino group of PCN to a neighboring molecule. A combination of high photophysical sensitivity of c-CN + toward its immediate environment and rich structural capabilities in assembling (c-CN) 2 2+ pairs in different crystal packings in a family of phases with the general formula (c-CN) 2 [M 2 (PPh 2 ) 2 Cl 4 ] allows one to fine-tune the luminescence properties of the latter. The results were rationalized as a variation of π−π intercationic spacings, which tunes the degree of excitedstate charge transfer between c-CN + cations. As a result, compounds with relatively short interplanar π−π-separation between the cations show a stronger charge-transfer-mediated bathochromic shift.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Pd(II)- and Pt(II)-Assisted P–C Activation/Cyclization Reactions with a Luminescent α-Aminophosphine

Afonin,

Martynenko,

Kolybalov

et al. 2023

Inorg. Chem.

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Recyclable Ag/GO-NH2 catalyzed multicomponent aminophosphinoylation of benzyl alcohols with amines and H-phosphine oxides

Huang,

Zhu,

Shi

et al. 2025

Tetrahedron

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Regioselective α-Phosphonylation of Unprotected Alicyclic Amines

Li,

Yu,

Chen

et al. 2024

Org. Lett.

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Unprotected alicyclic amines undergo α-C−H bond phosphonylation via a two-stage one-pot process involving the oxidation of aminederived lithium amides with simple ketone oxidants, generating transient imines which are then captured with phosphites or phosphine oxides. Amines with an existing α-substituent undergo regioselective α′-phosphonylation. Amine α-arylation and α′-phosphonylation can be combined, generating a difunctionalized product in a single operation.

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Phospha-Mannich reactions of phosphinous acids R ₂ P–OH and their derivatives

Cited by 6 publications

References 571 publications

Pd(II)- and Pt(II)-Assisted P–C Activation/Cyclization Reactions with a Luminescent α-Aminophosphine

Pd(II)- and Pt(II)-Assisted P–C Activation/Cyclization Reactions with a Luminescent α-Aminophosphine

Recyclable Ag/GO-NH2 catalyzed multicomponent aminophosphinoylation of benzyl alcohols with amines and H-phosphine oxides

Regioselective α-Phosphonylation of Unprotected Alicyclic Amines

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Phospha-Mannich reactions of phosphinous acids R 2 P–OH and their derivatives

Cited by 6 publications

References 571 publications

Pd(II)- and Pt(II)-Assisted P–C Activation/Cyclization Reactions with a Luminescent α-Aminophosphine

Pd(II)- and Pt(II)-Assisted P–C Activation/Cyclization Reactions with a Luminescent α-Aminophosphine

Recyclable Ag/GO-NH2 catalyzed multicomponent aminophosphinoylation of benzyl alcohols with amines and H-phosphine oxides

Regioselective α-Phosphonylation of Unprotected Alicyclic Amines

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Phospha-Mannich reactions of phosphinous acids R ₂ P–OH and their derivatives