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. Author manuscript; available in PMC: 2017 Sep 8.
Published in final edited form as: Angew Chem Int Ed Engl. 2014 Jul 14;53(36):9637–9639. doi: 10.1002/anie.201405594

Table 1.

Solution metathesis reactions of Ph2IOTf.

graphic file with name nihms898870u2.jpg
entry Ar’ time (h) ratio 3:4:1[b] yield[c]
a 4-Me-C6H4 24 9.8:28.5:1.0 48
b 4-MeO-C6H4 25 27.3:23.1:1.0 78
c 1-naphthyl 26 2.0:1.0:0.0 14
[a]

Conditions: 0.2 M solution of Ph2IOTf in (CH2Cl)2, 5 equiv aryl iodide, thick-walled glass tube sealed with a Teflon screwcap and immersed in an oil bath kept at 120–125 °C.

[b]

Molar ratios calculated by integration of 1H NMR spectra.

[c]

Percent yield after silica gel column chromatography (gradient 10% → 40% acetone-CH2Cl2) to remove nonpolar byproducts. The stated value is the sum of the yields of individual compounds present in the product mixture. A comparison of 1H NMR spectra of crude and purified reaction mixtures indicated that insignificant changes in the ratio of iodonium triflate products had occurred upon chromatography.