New chiral phosphorus-containing dendrimers with ferrocenes on the periphery

Turrin, Cédric‐Olivier; Chiffre, Jérôme; Daran, Jean‐Claude; Montauzon, Dominique de; Caminade, Anne‐Marie; Manoury, Éric; Balavoine, G.; Majoral, Jean‐Pierre

doi:10.1016/s0040-4020(01)00080-1

Cited by 64 publications

(40 citation statements)

References 48 publications

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“…203 The functionalised chiral ferrocene derivative 186 has been prepared by the Pd(OAc) 2 -catalysed reaction of 4-methoxyphenylboronic acid 184 with (S)-2-iodoferrocenecarboxaldehyde 185, which was introduced into the periphery of a phosphorous-containing chiral dendrimer by further sequential reactions (Scheme 75). 204 Zhang and co-workers used coloured dendrimers as soluble supports for the SM cross-coupling reaction. 205 Figure 12.…”

Section: Dendrimer Synthesis Via the Sm Cross-couplingmentioning

confidence: 99%

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Kotha¹,

Lahiri²,

Kashinath³

2002

Tetrahedron

1,646

530

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Section: Dendrimer Synthesis Via the Sm Cross-couplingmentioning

confidence: 99%

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Kotha¹,

Lahiri²,

Kashinath³

2002

Tetrahedron

1,646

530

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“…Dendrimers were synthesized in which the ferrocene unit was sequentially ensconced within successive dendrimer generations. To investigate the effect of ''burying'' the electroactive organometallic functionality, the known phosphorus-containing dendrimers of Majoral were used and ferrocenyl aldehyde endgroups were incorporated, which have planar chirality [29]. Additional dendrimer layers were added via condensation of a phosphorhydrazide H 2 NNMeP(S)Cl 2 and subsequent reaction with two equivalents of 4-hydroxybenzaldehyde sodium salt and the pendant PCl 2 group as shown in Scheme 2.…”

Section: Ferrocenyl Substituted In the Periphery Of Dendrimersmentioning

confidence: 99%

Where Organometallics and Dendrimers Merge: The Incorporation of Organometallic Species into Dendritic Molecules

2005

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This review will describe the ongoing efforts being made to incorporate organometallic fragments into the framework of dendrimers. While purely dendritic organic molecules are well known and well studied, species incorporating organometallic moieties potentially offer many benefits that are not available to only organic containing dendrimers. For example, catalytic or redox active organometallic functions can be included in the dendritic framework and impart these characteristics onto the dendrimer. This report will give an overview of the latest developments in this field by highlighting selected examples that detail novel synthetic strategies or dendrimer construction methodologies, interesting practical applications or address specific problems associated with organometallic dendrimers.

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“…The reaction proceeds in the same conditions than with methyl trifunctional core for the synthesis of dendrimers. [8] The Pϭ NϪP moieties of the PϭNϪPϭX linkage is very similar for flate, to afford compounds 9a and 10a, from 5a and 6a, …”

mentioning

confidence: 99%

N-Thiophosphorylated andN-Phosphorylated Iminophosphoranes [R3P=N–P(X)R′2; × = O, S] as Models for Dendrimers: Synthesis, Reactivity and Crystal Structures

Larré

Donnadieu

Caminade

et al. 1999

Eur. J. Inorg. Chem.

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Several R3P=N–P(X)R′2 and Fe[C5H4Ph2P=N–P(X)R′2]2 derivatives (X = S, O) are readily obtained from Staudinger reactions between phosphanes and N3–P(X)R′2. The P=N–P=X groups are easily alkylated on the × atom with methyl or isopropyl triflates. The alkylation induces a lengthening of the P–X bond, as shown by X‐ray diffraction studies. This corresponds to a weakening of the P–X bond which can be cleaved with P(NMe2)3 to yield [P=N–P:] linkages. The presence of tricoordinated phosphorus atoms opens the way to a versatile reactivity, including the reaction with alkyl iodides and functionalized azides. These molecules are good models for screening which types of reagents and reactions could be used with macromolecules possessing also P=N–P=X linkages, such as dendrimers.

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New chiral phosphorus-containing dendrimers with ferrocenes on the periphery

Cited by 64 publications

References 48 publications

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

Where Organometallics and Dendrimers Merge: The Incorporation of Organometallic Species into Dendritic Molecules

N-Thiophosphorylated andN-Phosphorylated Iminophosphoranes [R3P=N–P(X)R′2; × = O, S] as Models for Dendrimers: Synthesis, Reactivity and Crystal Structures

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