FULL PAPERS
Ligand Effects in the Gold Catalyzed Hydration of Alkynes
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Experimental Section
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Typical procedure for the acid free condition (condition A):
A glass vial equipped with a screw cap and a stir bar was
charged with 1-octyne 1a (112 mg, 150 mL, 1 mmol) dis-
solved in a mixture of MeOH (0.3 mL) and water (36 mL,
2 mmol). A stock solution of AgOTf (0.01M in methanol,
30 mL, 0.0003 mmol) and a stock solution of L4-Au-Cl
(0.01M in methanol, 20 mL, 0.0002 mmol) were introduced
to the reaction mixture. The reaction was stirred at 808C
and the progress of reaction was monitored by GC or
1H NMR. After the reaction was completed, the mixture
was filtered through a Celite plug, solvent evaporated and
the crude product purified by silica gel column chromatog-
raphy with EtOAc/hexanes (1:5) as eluent.
Typical procedure for acid co-catalyzed hydration (condi-
tion B): A glass vial equipped with a screw cap and a stir
bar was charged with 1-octyne 1a (112 mg, 150 mL, 1 mmol)
dissolved in 0.3 mL MeOH/water (25:1) mixture. A stock
solution of acid promoter TfOH (0.01M in methanol,
450 mL, 0.0045 mmol), a stock solution of AgOTf (0.01M in
methanol, 15 mL, 0.00015 mmol) and a stock solution of L4-
Au-Cl (0.01M in methanol, 10 mL, 0.0001 mmol) were intro-
duced to the reaction mixture. The reaction mixture was
stirred at room temperature and the progress of reaction
1
was monitored by GC or H NMR. After the reaction was
completed, the mixture is quenched with saturated bicar-
bonate and extracted with EtOAc. The organics are dried
over anhydrous sodium sulfate, filtered and solvent evapo-
rated using a rotary evaporator. The crude product is sub-
jected to silica gel column chromatography with EtOAc/hex-
anes (1:5) as eluent.
Acknowledgements
We are grateful to the National Science Foundation for finan-
cial support (CHE-1401700). B.X. is grateful to the National
Science Foundation of China for financial support (NSFC-
21472018).
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