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Beilstein J. Org. Chem. 2013, 9, 215–222, doi:10.3762/bjoc.9.25
Graphical Abstract
Figure 1: Schematic depiction of (a) a rigid phenylene-ethynylene polymer core with ligands attached via flex...
Figure 2: Generic structure of spacers containing an even (n = 1, 3) and an odd (n = 2, 4) number of units.
Figure 3: Synthetic strategy for rigid spacers with an even number of units.
Figure 4: Synthetic strategy for rigid spacers with an odd number of units.
Scheme 1: Synthesis of building blocks; (a) from 1, Pd(PPh3)4 , CuI, PPh3, TEA, toluene, 50 °C, 5 h, 31% for 3...
Scheme 2: Synthesis of a two-unit spacer. (a) PdCl2(PPh3)2, CuI, TEA, THF, microwave, 60 °C, 20 min, 81% for 7...
Scheme 3: Synthesis of three-unit spacers. (a) from 4: TBAF, THF, 62%; from 6 and 14: K2CO3, MeOH/CH2Cl2, 45 ...
Scheme 4: Synthesis of a four-unit spacer. (a) PdCl2(PPh3)2, CuI, TEA, THF, microwave, 60 °C, 20 min, 73%; (b...
Scheme 5: Synthesis of a five-unit spacer. (a) PdCl2(PPh3)2, CuI, TEA, THF, microwave, 60 °C, 20 min, 70%; (b...
Scheme 6: Synthesis of divalent ligand 22. (a) CuSO4·5H2O, Na-ascorbate, DMF/H2O, microwave, 80 °C, 40 min, 8...
Scheme 7: Synthesis of divalent ligand 24. (a) 13, TBAF in THF, rt, 1 h, then H2O, TBTA, CuSO4·5H2O, Na-ascor...
Figure 5: Previously tested compounds.
Beilstein J. Org. Chem. 2012, 8, 732–737, doi:10.3762/bjoc.8.82
Figure 1: The papulacandins.
Scheme 1: (a) H2SO4, MeOH, reflux, 18 h, 3: 98%; (b) BnBr, K2CO3, acetone, reflux, 18 h; (c) LiAlH4, THF, rt,...
Scheme 2: (a) NaOMe in MeOH, MeOH, rt, 1 h, 96%; (b) (t-Bu)2Si(OTf)2, pyridine, DMF, −40 °C to rt, 2 h, 90%; ...
Scheme 3: (a) Pd2(dba)3∙CHCl3, NaOt-Bu, toluene, 50 °C, 6–20 h, 23: 72%, 24: 79%, 25: 62%; (b) DiBAL-H, CH2Cl2...
Scheme 4: (a) Pd/C, NaHCO3, H2, THF, rt, 1.5 h, 98%; (b) MOMCl, DiPEA, DMAP, CH2Cl2, rt, 4 d, 78%; (c) TBAHF,...