Reaction SMILES: [C:1]([O:5][C:6](=[O:26])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12](B2OC(C)(C)C(C)(C)O2)=[C:11]([O:24][CH3:25])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:27]([O:31][C:32](=[O:88])[CH2:33][N:34]([CH2:80][C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])[CH2:35][C:36]1[CH:41]=[C:40](Br)[CH:39]=[C:38]([CH2:43][N:44]([CH2:71][CH2:72][C:73]2[CH:78]=[CH:77][C:76]([NH2:79])=[CH:75][CH:74]=2)[CH2:45][C:46]2[N:51]=[C:50]([CH2:52][N:53]([CH2:62][C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[CH2:54][C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH:49]=[C:48](Br)[CH:47]=2)[N:37]=1)([CH3:30])([CH3:29])[CH3:28].[C:89](=[O:92])([O-])[O-:90].[Cs+].[Cs+]>CN(C=O)C.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:27]([O:31][C:32](=[O:88])[CH2:33][N:34]([CH2:80][C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])[CH2:35][C:36]1[CH:41]=[C:40]([C:14]2[CH:13]=[CH:12][C:11]([O:24][CH2:25][C:89]([O:90][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:92])=[CH:10][C:9]=2[O:8][CH3:7])[CH:39]=[C:38]([CH2:43][N:44]([CH2:71][CH2:72][C:73]2[CH:78]=[CH:77][C:76]([NH2:79])=[CH:75][CH:74]=2)[CH2:45][C:46]2[N:51]=[C:50]([CH2:52][N:53]([CH2:62][C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[CH2:54][C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH:49]=[C:48]([C:12]3[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:26])=[CH:10][C:11]=3[O:24][CH3:25])[CH:47]=2)[N:37]=1)([CH3:30])([CH3:29])[CH3:28]
Reactant: O=C([O-])[O-]
Reactant: COc1cc(OCC(=O)OC(C)(C)C)ccc1B1OC(C)(C)C(C)(C)O1
Reactant: CC(C)(C)OC(=O)CN(CC(=O)OC(C)(C)C)Cc1cc(Br)cc(CN(CCc2ccc(N)cc2)Cc2cc(Br)cc(CN(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)n2)n1
Agent: c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Agent: [Cs+]
Solvent: CCOC(C)=O
Solvent: CN(C)C=O
Solvent: O
Product: COc1cc(OCC(=O)OC(C)(C)C)ccc1-c1cc(CN(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)nc(CN(CCc2ccc(N)cc2)Cc2cc(-c3ccc(OCC(=O)OC(C)(C)C)cc3OC)cc(CN(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)n2)c1
Temperature: 80 °C
Reaction time: 8 h

Procedure:
Compound 3 (0.11 g, 0.30 mmol) and tetra(tert-butyl)-2,2′,2″,2′″-{[2-(4-aminophenyl)ethylimino]-bis(methylene)bis(4-bromopyridine-6,2-diyl)bis(methylenenitrilo)}tetrakis(acetate) (0.10 mg, 0.10 mmol) were dissolved in dry DMF (5 ml) and the mixture was deaerated with argon. Caesium carbonate (0.11 g, 0.34 mmol) and tetrakis(triphenylphosphine)palladium (4.6 mg, 0.004 mmol) were added to the mixture and the reaction was stirred overnight at 80° C. The reaction mixture was cooled to room temperature and diluted with water (10 ml) and ethyl acetate (10 ml). Black particles were removed by filtration through a pad of Celite. The organic layer was separated, washed with brine (20 ml) and dried over sodium sulphate. The product was purified by flash chromatography on silica gel (first 5% methanol in dichloromethane and finally 10%). The yield was 90.0 mg (69%). 1H NMR (CDCl3, 500 MHz): δ 7.63-7.72 (4H, m), 7.24 (2H, s), 6.90 (2H, d), 6.55 (2H, d), 6.50 (2H, d), 6.41 (2H, s), 4.42 (4H, s), 4.08 (4H, s), 3.96 (4H, s), 3.83 (6H, s), 3.53 (8H, s), 2.68-2.97 (4H, m), 1.45 (54H, m).