Tris(1,1-dimethylethyl)phosphine → 2,2':6',2''-Terpyridine

HRID 1948838Notes

Reaction equation

HRID 1948838 reaction equation
C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[CH:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]3[N:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:21]=2)[N:17]=[CH:16][CH:15]=1.C#C.C([Sn](CCCC)CCCC)CCC>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]>[CH:28]1[CH:27]=[C:26]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([C:18]3[N:17]=[CH:16][CH:15]=[CH:14][CH:19]=3)[N:21]=2)[N:31]=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 131730346HCID 131730346, compound

Product 1

HCID 708482,2':6',2''-TerpyridineYield 84%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Inside the glove box, 130 mg of PDI-Br (1 eq, Mw=665.62 gr/mole, n=1.95×10−4 mole) were weighed in a clean vial. 14.65 mg of Pd2(DBA)3, (0.05 eq) (10% mole, Mw=915.72 gr/mole, n=1.6×10−5 mole) & 10% mole of tri-(t-Butyl)phosphine (6.75 mg, Mw=211.3902 gr/mole) were added to PDI-Br dissolved in 10 ml of toluene. The mixture was stirred for 5 min & then added dropwise to a toluenic solution of Terpy-acetylene-tributylTin. According to the TLC, the reaction is completed in 2 h. Silica gel column chromatography resulted in 231 mg (Mw=918.09 gr/mole) of the product, Terpy-PDI(dmp), 84% yield. Mass-spectra and NMR confirm that the product was obtained as presented in FIG. 15.

Workup

  1. waitthe reaction is completed in 2 h

Sources & evidence

ORD record
ord-db0586b690674137ad21142ad07b95d9
Source dataset
uspto-grants-2013_03
Patent number
US08399670B2

Reaction notes

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