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23rd August 2013 @ 14:32

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Reaction information

*#Reaction file
reactionscheme_17 .cdx
*Reaction file type CDX
*Procedure A small Schlenk tube containing 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl) benzene (47 mg, 54 μmol), 1-Acetylthio-4-iodobenzene (33 mg, 0.12 mmol, 2.20 eq.), PdCl2 (1 mg, 5 μmol, 10 mol%), PPh3 (3 mg, 0.01 mmol, 20 mol%) and CuI (2 mg, 0.01 mmol, 20 mol%), with stirring, was evacuated under HV and refilled with Ar before adding THF (2.0 mL: approx. 40 mL/mmol). EDIA (0.06 mL, 42 mg, 0.32 mmol, 6.00 eq.) was then added dropwise. The reaction mixture was stirred at r.t. for 14 h; the disappearance of starting material (Rf 0.02, (20/1) hexane/DCM) was monitored by TLC. The solvent was evaporated and the residue was dissolved in DCM; the solution was washed with water and brine and dried over MgSO4, to afford, after evaporation of the solvent, the crude product (86 mg). The solid (orangish, 41 mg) obtained by column chromatography on silica gel, with eluent (3/1) DCM/hexane, was found to be a mixture of product and unreacted  1-Acetylthio-4-iodobenzene (both Rf 0.56): further chromatographic purification was not attempted because of evidence (by 2D- TLC) of decomposition of the product on silica. The pure product (26 mg, 22 μmol, yield 41%) was obtained as orangish solid by precipitation from hexane/DCM.  
*Yield (%) 41 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p13.pdf
PhD Thesis - 16Sep2010_final p114-115.pdf
Further information Compound 17: 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(4-thioacetylphenyl)ethynyl)phenyl) ethynyl)phenyl)ethynyl)benzene

For multistep reactions (or their steps):

Overall reaction? False
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step

Overall reaction 4: 1-acetylthio-4-iodobenzene

Reaction 15: Deprotection of 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene: 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl) benzene

For step in multistep reaction - link to following reaction step  
Attached Files
PhD Thesis - 16Sep2010_final p114-115.pdf
reactionscheme_17 .cdx