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19th August 2013 @ 14:39

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Reaction information

*#Reaction file
reactionscheme_34.cdx
*Reaction file type CDX
*Procedure A 25 mL Schlenk flask containing 1,4-dibromonitrobenzene (228 mg, 0.81 mmol), (2-(4-Ethynylphenylthio)ethyl)trimethylsilane (418 mg, 1.78 mmol, 2.20 eq.), PdCl2 (7 mg, 0.04 mmol, 5 mol%), PPh3 (21 mg, 0.08 mmol,  10 mol%) and CuI (15 mg, 0.08 mmol, 10 mol%), with stirring, was evacuated under HV and refilled with Ar before adding distilled benzene (10 mL). Triethylamine, TEA (0.68 mL, 492 mg, 4.86 mmol, 6.00 eq.) was then added dropwise, and the reaction mixture was stirred at 70 °C for 5 h; the disappearance of starting materials was monitored by TLC. The solvent was evaporated, the residue was dissolved in DCM and the solution was washed with water and brine and dried over MgSO4; evaporation of the solvent afforded the crude product (637 mg), dark oil containing bright yellow solid. This was column chromatographed on silica gel using as eluent (4/1) hexane/DCM, yielding the homocoupling dimer 1,4-bis(4-(2-(trimethylsilyl)ethylthio)phenyl)buta-1,3-diyne (yellow solid, 81 mg, 0.17 mmol, yield 21%; Rf 0.33) 
*Yield (%) 21 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p16.pdf
 
PhD Thesis - 16Sep2010_final p124-125.pdf
Further information Compound 34: 1,4-bis(4-(2-(trimethylsilyl)ethylthio)phenyl)buta-1,3-diyne

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 Reaction 32: Deprotection of (2-(Trimethylsilyl)ethyl)(4-(2-(trimethylsilyl)ethynyl)phenyl)sulfane: (2-(4-ethynylphenylthio)ethyl)trimethylsilane
For step in multistep reaction - link to following reaction step  
Attached Files
PhD Thesis - 16Sep2010_final p124-125.pdf
reactionscheme_34.cdx