Synthesis of Precursors of 4‐Phosphino‐1<i>H</i>‐pyrrole‐3‐carbaldehyde Derivatives

Smaliy, Radomyr V.; Chaykovskaya, Aleksandra A.; Shtil, N. A.; Savateev, Aleksandr S.; Kostyuk, Alexander

doi:10.1002/hc.21069

Cited by 3 publications

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References 18 publications

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“…Tris( N -pyrrolyl)phosphine , is a weak electron donor and good π-acceptor ligand, which has been successfully applied in hydroformylation reactions. − The C2-connected structural isomer, tris(1-methylpyrrol-2-yl)phosphine, was first reported in 1974, followed by several derivatives of (1-methylpyrrol-2-yl)phosphines. − Yet, the properties of these phosphines have barely been investigated. , Among them, the cataCXium ligands represent a prominent class of N -arylated pyrrolylphosphines, which have been used in Suzuki cross-coupling reactions . Few reports exist about C3-bound pyrrolylphosphines. ,,− In fact, the only representative with three pyrrolyl groups, tris(1- tert -butylpyrrol-3-yl)phosphine, has been generated in situ but was not isolated, and the electronic properties were not investigated . Note that the structurally related (indol-3-yl)phosphines are powerful ligands for Pd-catalyzed cross-coupling reactions. ,− Herein, we report the synthesis and properties of a series of (1,2,5-trimethylpyrrolyl)phosphines that, consistent with Zipse’s prediction, are strongly electron-donating arylphosphines.…”

Section: Introductionmentioning

confidence: 99%

1,2,5-Trimethylpyrrolyl Phosphines: A Class of Strongly Donating Arylphosphines

et al. 2023

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Arylphosphines are among the most important ligands in coordination chemistry and catalysis but are generally inferior to alkylphosphines when strong electron donor properties are required. Herein, we report the synthesis and properties of 1,2,5-trimethylpyrrolyl phosphines and show that their electrondonating ability can exceed that of alkylphosphines. The new phosphines can be prepared on a multi-gram scale in one-pot procedures starting from commercially available reagents. Tris-(1,2,5-trimethyl)pyrrolylphosphine P(tmp) 3 is a crystalline solid, displays a Tolman electronic parameter (TEP) of 2055.0 cm −1 and can be handled in air. Nickel(0), palladium(II), gold(I), and ruthenium(II) complexes with 1,2,5-trimethylpyrrolyl-based phosphines are reported in addition to preliminary investigations on the use of P(tmp) 3 in ruthenium-catalyzed olefin metathesis.

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Section: Introductionmentioning

confidence: 99%

1,2,5-Trimethylpyrrolyl Phosphines: A Class of Strongly Donating Arylphosphines

et al. 2023

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“…N ‐substituted pyrroles are known to be readily phosphanylated with phosphane halides, affording phosphanes III (X = lone pair), which are potential substrates for further electrophilic formylation. Recently, we have shown that formylation of phosphane III (X = lone pair) and its derivatives (X = O, S, Se) under Vilsmeier–Haack conditions led to the same product— phosphane oxides IV .…”

Section: Introductionmentioning

confidence: 98%

A Simple Approach to Vicinal Pyrrolylphosphane Aldehydes

Savateev

Shtil

Chaikovskaya

et al. 2014

Heteroatom Chemistry

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A simple approach to vicinal pyrrolylphosphane aldehydes was developed. The reaction of Alder's dimer 1 with a set of pyrrolylphosphane derivatives—its oxides, sulfides, and selenides—was studied in detail. While Alder's dimer reacted with phosphane oxides and sulfides at the O and S atoms, phosphane selenides 4a–c were found to be suitable for the introduction of the formyl group into the pyrrole ring. The reaction of highly electrophilic Alder's dimer with pyrrolylphosphane selenides proceeded predominantly at the pyrrolyl nuclei, affording the corresponding aldehydes. The phosphoroselenoyl groups of aldehydes 11 were reduced either with Raney Ni or hexamethylphosphorustriamide under mild conditions, affording pyrrolylphosphane aldehydes 12.

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ChemInform Abstract: Synthesis of Precursors of 4‐Phosphino‐1H‐pyrrole‐3‐carbaldehyde Derivatives.

et al. 2013

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Synthesis of Precursors of 4-Phosphino-1H-pyrrole-3-carbaldehyde Derivatives.-Two pathways for the synthesis of 4-(diphenylphosphoryl)-1H-pyrrole-3-carbaldehyde (III) are developed. The formyl fragment of (III) is converted into a Schiff base (V), followed by the reduction of the phosphoryl group to phosphine (VI). -(SMALIY, R.; CHAYKOVSKAYA, A. A.; SHTIL, N. A.; SAVATEEV, A. S.; KOSTYUK*, A. N.; Heteroat. Chem. 24 (2013) 2, 146-151, http://dx.doi.org/10.1002/hc.21069 ; Inst. Org. Chem., Acad. Sci. Ukr., Kiev 02660, Ukraine; Eng.) -H. Toeppel 29-194

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Synthesis of Precursors of 4‐Phosphino‐1H‐pyrrole‐3‐carbaldehyde Derivatives

Abstract: In this work, possible approaches to the synthesis

Cited by 3 publications

References 18 publications

1,2,5-Trimethylpyrrolyl Phosphines: A Class of Strongly Donating Arylphosphines

1,2,5-Trimethylpyrrolyl Phosphines: A Class of Strongly Donating Arylphosphines

A Simple Approach to Vicinal Pyrrolylphosphane Aldehydes

ChemInform Abstract: Synthesis of Precursors of 4‐Phosphino‐1H‐pyrrole‐3‐carbaldehyde Derivatives.

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