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1 article(s) from Pertici, Francesca

Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors

Francesca Pertici,
Norbert Varga,
Arnoud van Duijn,
Matias Rey-Carrizo,
Anna Bernardi and
Roland J. Pieters

Beilstein J. Org. Chem. 2013, 9, 215–222, doi:10.3762/bjoc.9.25

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Graphical Abstract

Figure 1: Schematic depiction of (a) a rigid phenylene-ethynylene polymer core with ligands attached via flex...

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Figure 2: Generic structure of spacers containing an even (n = 1, 3) and an odd (n = 2, 4) number of units.

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Figure 3: Synthetic strategy for rigid spacers with an even number of units.

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Figure 4: Synthetic strategy for rigid spacers with an odd number of units.

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Scheme 1: Synthesis of building blocks; (a) from 1, Pd(PPh₃)₄ , CuI, PPh₃, TEA, toluene, 50 °C, 5 h, 31% for 3...

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Scheme 2: Synthesis of a two-unit spacer. (a) PdCl₂(PPh₃)₂, CuI, TEA, THF, microwave, 60 °C, 20 min, 81% for 7...

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Scheme 3: Synthesis of three-unit spacers. (a) from 4: TBAF, THF, 62%; from 6 and 14: K₂CO₃, MeOH/CH₂Cl₂, 45 ...

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Scheme 4: Synthesis of a four-unit spacer. (a) PdCl₂(PPh₃)₂, CuI, TEA, THF, microwave, 60 °C, 20 min, 73%; (b...

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Scheme 5: Synthesis of a five-unit spacer. (a) PdCl₂(PPh₃)₂, CuI, TEA, THF, microwave, 60 °C, 20 min, 70%; (b...

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Scheme 6: Synthesis of divalent ligand 22. (a) CuSO₄·5H₂O, Na-ascorbate, DMF/H₂O, microwave, 80 °C, 40 min, 8...

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Scheme 7: Synthesis of divalent ligand 24. (a) 13, TBAF in THF, rt, 1 h, then H₂O, TBTA, CuSO₄·5H₂O, Na-ascor...

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Figure 5: Previously tested compounds.

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Published 31 Jan 2013

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