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Issue 5, 2016
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Polyphosphazenes for the Stille reaction: a new type of recyclable stannyl reagent

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Abstract

A random phosphazene copolymer {[N[double bond, length as m-dash]P((CH2)7–Br)Ph]0.5[N[double bond, length as m-dash]PMePh]0.5}n (2) and a block copolyphosphazene {[N[double bond, length as m-dash]P((CH2)7–Br)Ph]0.5[N[double bond, length as m-dash]PMePh]0.5}45-b-[N[double bond, length as m-dash]P(O2C12H8)]55 (5), having a branch with two randomly distributed units, have been synthesized and used as precursors for the stannyl derivatives {[N[double bond, length as m-dash]P((CH2)7–SnBu2An)Ph]0.5[N[double bond, length as m-dash]PMePh]0.5}n (3) and {[N[double bond, length as m-dash]P((CH2)7–SnBu2An)Ph]0.5[N[double bond, length as m-dash]PMePh]0.5}45-b-[N[double bond, length as m-dash]P(O2C12H8)]55 (6, An = p-MeOC6H4). Polymers 3 and 6 were tested as recyclable tin reagents in the Stille cross-coupling reaction with ArI, using various Pd catalysts and different experimental conditions. Polymer 6 can be recycled without a significant release of tin, but its efficiency decreased after three consecutive cycles. This effect was explained by studying the self-assembly of the polymer under the same conditions used for the catalytic experiments, which evidenced the progressive coalescence of the polymeric vesicles (polymersomes) leading to stable and bigger core–shell aggregates by the attraction of the [N[double bond, length as m-dash]P(O2C12H8)] rich membranes, thus decreasing the accessibility of the tin active centers.

Graphical abstract: Polyphosphazenes for the Stille reaction: a new type of recyclable stannyl reagent

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Publication details

The article was received on 14 Jul 2015, accepted on 02 Nov 2015 and first published on 02 Nov 2015


Article type: Paper
DOI: 10.1039/C5DT02670A
Citation: Dalton Trans., 2016,45, 2227-2236
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    Polyphosphazenes for the Stille reaction: a new type of recyclable stannyl reagent

    S. Martínez-Arranz, D. Presa-Soto, G. A. Carriedo, A. Presa Soto and A. C. Albéniz, Dalton Trans., 2016, 45, 2227
    DOI: 10.1039/C5DT02670A

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