Cesium carbonate → 21H,22H-Porphine

HRID 2220776Notes

Reaction equation

HRID 2220776 reaction equation
Br[C:2]1[C:3]2[NH:7][C:6]([C:8](C3C=C(C(C)(C)C)C=C(C(C)(C)C)C=3)=[C:9]3[N:40]=[C:12]([C:13](Br)=[C:14]4[NH:38][C:17](=[C:18](C5C=C(C(C)(C)C)C=C(C(C)(C)C)C=5)[C:19]5[CH:20]=[CH:21][C:22]=1[N:23]=5)[CH:16]=[CH:15]4)[CH:11]=[CH:10]3)=[CH:5][CH:4]=2.C1C=C2C=CC(O)=C(C3C4C(=CC=CC=4)C=CC=3O)C2=CC=1.C1C=CC(P(C2C(OC3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=CC=3)=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[C:3]12[CH:2]=[C:22]3[N:23]=[C:19]([CH:20]=[CH:21]3)[CH:18]=[C:17]3[NH:38][C:14]([CH:15]=[CH:16]3)=[CH:13][C:12]3=[N:40][C:9]([CH:10]=[CH:11]3)=[CH:8][C:6]([NH:7]1)=[CH:5][CH:4]=2

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 11762BinolHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 178440595HCID 178440595, compound

Product 1

HCID 13770524121H,22H-Porphine

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The general procedure was used to couple 5,15-dibromo-10,20-di(3,5-di-tert-butylphenyl)porphyrin (0.043 g, 0.05 mmol) with R-(+)-1,1′-bi-2-naphthol (0.167 g, 0.58 mmol), using Pd2(dba)3 (0.0046 g, 0.005 mmol) and DPEphos (0.0107 g, 0.02 mmol) in the presence of Cs2CO3 (0.0652 g, 0.2 mmol). The reaction was conducted in toluene (5 mL) at 100° C. for 20 h. The title compound was isolated by flash column chromatography (silica gel, ethyl acetate:hexanes (v/v)=1:5) as purple solids (0.022 g, 35%). 1H NMR (300 MHz, CDCl3): δ 9.21 (d, J=4.8 Hz, 4H), 8.77 (d, J=4.8 Hz, 4H), 7.37-8.05 (m, 26H), 7.07 (d, J=16.2 Hz, 2H), 6.49 (d, J=9.6 Hz, 2H), 5.66 (s, 2H), 1.51 (m, 36H), −2.45 (s, 2H). 13C NMR (75 MHz, CDCl3): δ 161.2, 151.9, 149.0, 140.0, 134.4, 133.9, 131.7, 130.8, 130.3, 129.7, 129.6, 128.9, 128.6, 128.4, 127.9, 127.4, 127.0, 125.2, 125.0, 123.7, 121.3, 117.8, 117.2, 114.5, 35.0, 31.7. UV-vis (CHCl3, λmax, nm): 425, 521, 558, 598, 655. HRMS-MALDI ([M+H]+): calcd for C88H79N4O4, 1255.6096, found 1255.6045 with an isotope distribution pattern that is the same as calculated one.

Sources & evidence

ORD record
ord-9bb0ad10814647fbaa8e7934be7c774c
Source dataset
uspto-grants-2008_08
Patent number
US07417142B2

Reaction notes

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