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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 3.

Metathesis reactions of iodonium triflates 7.

graphic file with name nihms898870u4.jpg
entry Ar Ar’ ratio 6:4:7:(other)[b] yield[c]
a[d] Ph Ph 12.9[e]:1.0:(−)[f] 65
b[d] 4-MeC6H4 1.0:1.3:0.0:(−)[f] 73
c[d] 4-MeOC6H4 60.1:35.1:1.0:(−)[f] 76
d[d] 1-naphthyl 33.3:5.9:1.0:(−)[f] 59
e[d] 4-MeOC6H4 Ph 11.5:8.2:1.0:(1.0)[g] 60
f[d] 4-MeC6H4 1.3:1.0:0.0:(−)[f] 79
g[d] 4-MeOC6H4 6.9[e]:1.0:(−)[f] 89
h[d] 1-naphthyl 8.4:1.2:1.2:(1.0+0.6)[h] 64
i[d] mesityl 4-MeC6H4 1.0:7.0:0.0:(−)[f] 26
j[d] 4-MeOC6H4 1.0:13.0:0.0:(−)[f] 37
k[d] 1-naphthyl 1.0:8.4:8.4:(−)[i] 27
[a], [b], [c]

: same as in Table 1.

[d]

Reaction time: 12 h.

[e]

Compounds 7 and 4 are identical in this case.

[f]

Other products — if at all detectable — were present in insignificant amounts.

[g]

This other product was bis-(4-anisyl)iodonium triflate (1H-NMR, MS), perhaps arising as per ref. 1.

[h]

The major other product was 1-naphthyl-4-nitrophenyl-iodonium triflate; the minor other product was bis-(4-anisyl)iodonium triflate (1H-NMR, MS).

[i]

A trace amount of 1-naphthyl-4-nitrophenyl-iodonium triflate, too small to be measured accurately, was apparent by 1H-NMR and MS.