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Sonogashira Coupling of 4-Iodoanisole to Propargyl Alcohol; 3-(4-Methoxyphenyl)prop-2-yn-1-ol 

SyntheticPage 507
DOI: 10.1039/SP507
Submitted Sep 24, 2011, published Sep 28, 2011
Christopher Kelly (christopher.b.kelly@uconn.edu)
A contribution from Leadbeater Group


			Reaction Scheme: <IMG src="/images/empty.gif">Sonogashira Coupling&nbsp;of <SPAN id=csm1317576580386 class=csm-chemical-name title=4-Iodoanisole grpid="2">4-Iodoanisole</SPAN> to <SPAN id=csm1317576549829 class="csm-chemical-name csm-not-validated" title="Propargyl Alcohol" grpid="1">Propargyl Alcohol</SPAN><IMG src="/images/empty.gif">

Chemicals Used

4-Iodoanisole (98%,  Purchased from Sigma-Aldrich)
Propargyl Alcohol (99%, Purchased from Sigma-Aldrich)
Copper(I) Iodide (99.5% Purum, Purchased from Sigma-Aldrich)
Bis(triphenylphosphine)palladium(II) dichloride (> 99% Pure, Purchased from Sigma-Aldrich)
Triethylamine (99%, Purchased from ACROS)

 

Procedure

To a 250 mL round bottom flask equipped with stirbar was added 4-iodoanisole, ( 4.68 g, 0.020 mol, 1 equiv.) and Et3N (150 mL, 0.134 M in the iodide).  The solution was placed under a nitrogen atmosphere via a gas inlet adapter. To this solution was added PdCl2(PPh3)2 (0.702 g, 0.001 mol, 0.05 equiv.) and CuI (0.191 g, 0.001 mol, 0.05 equiv) all at once turning the solution yellow. Propargyl alcohol (1.46 g, 0.026 mol, 1.3 equiv) was then added all at once, turing the solution a cloudy green. The solution was stirred for 18 hours at room temperature and monitored by TLC (8:2 Hex: EtOAc). Upon completion of this time, the solution was filtered through Celite®, eluting with ethyl acetate. The filterate was then further diluted with  EtOAc (≈50 mL) and deionized water (≈100 mL) and the layers were seperated. The aqueous layer was extracted three times with EtOAc. The combine organic layers were dried with Na2SO4 and the solvent was removed in vacuo yielding a thick dark liquid. Purification was accomplished by flash column chromoatgraphy (Gradient 9:1 Hex: EtOAc to 8:2) affording pure 6r as a tan powdery solid (2.75 g, 85% yield). 

Author's Comments

Data

1H NMR (CDCl3, 300 MHz) d ppm 1.65 (t, J = 6.14 Hz, 1 H) 3.81 (s, 3 H) 4.48 (d, J = 6.14 Hz, 2 H) 6.84 (d, J = 9.10 Hz, 2 H) 7.38 (d, J = 8.77 Hz, 2 H) 13C NMR (CDCl3, 101 MHz) d ppm 51.85 (CH2) 55.53 (CH3) 85.82 (C) 86.22 (C) 114.21 (CH) 114.91 (C) 133.44 (CH) 159.95 (C)

Lead Reference

Belot, A.; Vogt, K. A.; Besnard, C.; Krause, N.; Alexakis, A. Angew. Chem. Int . Ed. 2009 , 48 , 8923.

Supplementary Information

H NMR (Alkyne OH HNMR.pdf)
C13 NMR (Alkyne OH C13.pdf)

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Keywords: alcohols, alkyl/alkenyl/aryl halides, alkynes, aromatics/arenes, Bis(triphenylphosphine)palladium(II) dichloride, Copper(I) Iodide, organometallics, oxidative addition, reductive elimination, transition metal catalysed

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