New functionalised ditertiary phosphines via phosphorus based Mannich condensation reactions

Durran, Sean E.; Elsegood, Mark R. J.; Hawkins, Neil; Smith, Martin B.; Talib, Salem

doi:10.1016/s0040-4039(03)01273-5

Cited by 32 publications

(44 citation statements)

References 10 publications

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“…1) and confirms single condensation has resulted. The geometry about P(1) is pyramidal as expected and bond lengths/angles are similar to those in other crystallographically characterised carboxylic acid modified phosphines [32,34,35,41]. …”

Section: Synthesis and Characterisationsupporting

confidence: 77%

“…We have previously found that Mannich based condensation reactions are extremely facile for the syntheses of functionalised tertiary and ditertiary phosphines [29][30][31][32][33][34]. Carboxylic acid phosphines [32,34] can be prepared by this procedure and furthermore, we have shown some of these ligands serve as convenient building blocks for the preparation of linear, dinuclear gold(I) complexes [35] with unusual finite and infinite structures.…”

Section: Synthesis and Characterisationmentioning

confidence: 95%

“…Carboxylic acid phosphines [32,34] can be prepared by this procedure and furthermore, we have shown some of these ligands serve as convenient building blocks for the preparation of linear, dinuclear gold(I) complexes [35] with unusual finite and infinite structures. In order to further understand the supramolecular capability of these ligands we turned our attention to half-sandwich organometallic compounds based on ruthenium(II).…”

Section: Synthesis and Characterisationmentioning

confidence: 99%

“…We are unaware of any systematic studies exploring the supramolecular chemistry of RuCl 2 (p-cymene)(PR 3 ) with phosphines from a similar ligand library. As part of ongoing studies in our group [29][30][31][32][33][34][35] we have used Mannich-based condensation reactions as an excellent procedure for synthesising highly functionalised tertiary and ditertiary phosphines. Herein we describe the use of isomeric, carboxylic acid or mixed phenol/carboxylic acid containing tertiary phosphines, Ph 2 PCH 2 Y, for the preparation of a range of RuCl 2 (p-cymene)(Ph 2 PCH 2 Y) complexes.…”

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confidence: 99%

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Supramolecular chemistry of half-sandwich organometallic building blocks based on RuCl2(p-cymene)Ph2PCH2Y

Dann

Durran

Elsegood

et al. 2006

Journal of Organometallic Chemistry

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Section: Synthesis and Characterisationsupporting

confidence: 77%

Section: Synthesis and Characterisationmentioning

confidence: 95%

Section: Synthesis and Characterisationmentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Supramolecular chemistry of half-sandwich organometallic building blocks based on RuCl2(p-cymene)Ph2PCH2Y

Dann

Durran

Elsegood

et al. 2006

Journal of Organometallic Chemistry

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“…Furthermore, these very mild conditions allows for the presence of several unprotected functional groups like carboxylic acids, alcohols, phenols, esters and alkenes. [33] The most commonly used hydroxymethylphosphine reagent has been the diphenyl derivative. In solution it has been applied in the synthesis of spectacular dendritic structures, [34][35][36][37] as well as of more simple phosphine ligands made from amino acids [38,39] and aminopyridines.…”

Section: Resultsmentioning

confidence: 99%

Efficient Solid‐Phase Synthesis of Peptide‐Based Phosphine Ligands: Towards Combinatorial Libraries of Selective Transition Metal Catalysts

Christensen

Meldal

2005

Chemistry A European J

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A new methodology for the solid-phase synthesis of peptide-based phosphine ligands has been developed. Solid supported peptide scaffolds possessing either primary or secondary amines were synthesised using commercially available Fmoc-protected amino acids and readily available Fmoc-protected amino aldehydes for reductive alkylation, in standard solid-phase peptide synthesis (SPPS). Phosphine moieties were introduced by phosphinomethylation of the free amines as the final solid-phase synthetic step, immediately prior to complexation with palladium(II), thus avoiding tedious protection/deprotection of the phosphine moieties during the synthesis of the ligands. The extensive use of commercial building blocks and standard SPPS makes this methodology well suited for the generation of solid-phase combinatorial libraries of novel ligands. Furthermore, it is possible to generate several different phosphine ligand libraries for every peptide scaffold library synthesised, by functionalising the scaffold libraries with different phosphine moieties. The synthesised ligands were characterised on solid support by conventional (31)P NMR spectroscopy and, cleaved from the support, as their phosphine oxides by HPLC, (1)H NMR, (31)P NMR and high resolution ESMS. Palladium(II) allyl complexes were generated from the resin bound ligands and to demonstrate their catalytic properties, palladium catalysed asymmetric allylic substitution reactions were performed. Good yields and moderate enantioselectivity was obtained for the selected combination of catalysts and substrate, but most importantly the concept of this new methodology was proven. Screening of ligand libraries should afford more selective catalysts.

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Mannich Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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This reaction is a multicomponent condensation between an amine, an enolizable carbonyl compound (donor), and a nonenolizable carbonyl compound (acceptor) to form a β‐amino carbonyl compound (ketone or ester), with the concomitant formation of both carbon‐carbon and carbon‐nitrogen bonds and is known as the Mannich reaction, or Mannich condensation. Several variants of this reaction have been discussed. The Mannich reaction occurs under very simple conditions and gives desired compounds in high yields with two potential chiral centers. This reaction has been extensively modified beside the variant reactions. Several conditions of this reaction have been discussed to enhance stereoselectivity as well as the final yield. This reaction has been used for the preparation of stereoselective compounds under catalytic conditions.

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New functionalised ditertiary phosphines via phosphorus based Mannich condensation reactions

Cited by 32 publications

References 10 publications

Supramolecular chemistry of half-sandwich organometallic building blocks based on RuCl2(p-cymene)Ph2PCH2Y

Supramolecular chemistry of half-sandwich organometallic building blocks based on RuCl2(p-cymene)Ph2PCH2Y

Efficient Solid‐Phase Synthesis of Peptide‐Based Phosphine Ligands: Towards Combinatorial Libraries of Selective Transition Metal Catalysts

Mannich Reaction

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