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9th August 2013 @ 12:21

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SOURCE

Author 1 is the author of this LabTrove post (and has contributor role of "Abstracter").

  *First name *Last name Email Organization Role
Author 2 Francesco Giustiniano   University of Southampton Doer
Author 3 Richard Whitby   University of Southampton Conceiver
Author 4          

TEXT

*Procedure or Transformation Sonogashira Coupling
*Compound(s) being made 1,4-bis(4-(2-(trimethylsilyl)ethylthio)phenyl)buta-1,3-diyne
*Chemicals used (delimited by semicolons ;) (2-(4-Ethynylphenylthio)ethyl)trimethylsilane1,4-dibromonitrobenzene PdCl2PPh3CuIbenzenetriethylamine
*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) 
*Authors Comments The crude product was column chromatographed yielding the pure 1-(2-(Trimethylsilyl)ethylthio)-4-(2-(4-(2-(4-(2-(trimethylsilyl)ethylthio) phenyl)ethynyl)-3-nitrophenyl)ethynyl)benzene (yield 41%; Rf 0.08), the homocoupling dimer 1,4-bis(4-(2-(Trimethylsilyl)ethylthio)phenyl)buta-1,3-diyne (yield 21%; Rf 0.33) and the monocoupling byproduct (2-(4-(2-(4-Bromo-2-nitrophenyl)ethynyl)phenylthio)ethyl)trimethylsilane (yield 36%; Rf 0.17).
Lead Reference Taken from: F. Giustiniano, 2010, "Directed Assembly of Functional Patterns",PhD thesis, University of Southampton. Pages 16, 124-125
Other References  
Multimedia Content  
*Data  1H NMR(300 MHz, CDCl3); 13C NMR (75 MHz, CDCl3)
#Data file 1
H NMR 34 - ju0706fg3 .jdx
#Data file 2
C NMR 34 - ju0706fg3 .jdx
#Data file 3  
#Data file 4  
#Data file 5  

SCHEME

*#Structure file (ChemDraw, ChemSketch or RXN file)
reactionscheme_34.cdx
*#Image file (GIF or PNG)
reactionscheme_34.gif

Keywords

Compounds Keywords Aromatics; alkynes
Reactions Keywords substitution
Other Keywords  
Attached Files
PhD Thesis - 16Sep2010_final p16.pdf
reactionscheme_34.cdx
reactionscheme_34.gif