Page 13 of 15
The Journal of Organic Chemistry
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mesityl(3ꢀ(trifluoromethyl)phenyl)iodonium trifluoromethanesulfonate (3ad).20 GP2 was used on a 5 mmol scale. Purification by
recrystallization in diethyl ether to afford the product as brown solids (1.24 g, 46%). Mp. 180ꢀ182 °C (Lit. 181ꢀ183 °C)20 1H NMR (400
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MHz, CDCl3) δ 7.94 (d, J = 8.4 Hz, 1H), 7.91 (s, 1H), 7.77 (d, J = 7.8 Hz, 1H), 7.54 (t, J = 8.0 Hz, 1H), 7.12 (s, 2H), 2.63 (s, 6H), 2.36 (s,
3H). 13C{1H}NMR (101 MHz, CDCl3) δ 144.9, 142.7, 134.2 (d, J = 33.8 Hz), 132.5, 130.6, 129.8 (d, J = 4.0 Hz), 128.6 (d, J = 3.7 Hz),
123.9, 121.2, 121.0, 120.2 (q, J = 319.2 Hz), 112.1, 27.2 21.3. 19F NMR (376 MHz, CDCl3) δ ꢀ63.05, ꢀ78.53.
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mesityl(3ꢀnitrophenyl)iodonium trifluoromethanesulfonate (3ae). GP2 was used on a 5 mmol scale. Purification by recrystallization in
diethyl ether to afford the product as brown solids (1.19 g, 46%). Mp. 162ꢀ164 °C. 1H NMR (400 MHz, DMSOꢀd6) δ 8.82 (t, J = 2.0 Hz,
1H), 8.42 (ddd, J = 8.2, 2.2, 0.9 Hz, 1H), 8.18 (ddd, J = 8.0, 1.8, 0.9 Hz, 1H), 7.75 (t, J = 8.2 Hz, 1H), 7.26 (s, 2H), 2.61 (s, 6H), 2.32 (s,
3H). 13C{1H}NMR (101 MHz, DMSOꢀd6) δ 148.6, 143.6, 141.9, 139.7, 132.9, 130.0, 128.9, 126.4, 122.7, 120.7 (q, J = 322.1 Hz), 114.1,
26.4, 20.6. HRMS (ESI) calculated for C15H15INO2 [MꢀOTf]+: 368.0142, found: 368.0154.
(2ꢀchlorophenyl)(mesityl)iodonium trifluoromethanesulfonate (3af).21 GP2 was used on a 5 mmol scale. Purification by recrystallization in
diethyl ether to afford the product as brown solids (1.24 g, 49%). Mp. 171ꢀ172 °C (Lit. 167ꢀ168 °C)21 1H NMR (399 MHz, CDCl3) δ 7.62
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(dd, J = 8.0, 1.5 Hz, 1H), 7.53 (td, J = 7.7, 1.4 Hz, 1H), 7.29 (td, J = 7.8, 7.4, 1.5 Hz, 1H), 7.17 (s, 2H), 7.09 (dd, J = 8.2, 1.4 Hz, 1H),
2.62 (s, 6H), 2.40 (s, 3H). 13C{1H}NMR (100 MHz, CDCl3) δ 145.4, 143.0, 135.5, 133.5, 132.5, 131.4, 131.0, 130.6, 120.8, 120.4 (q, J =
319.9 Hz), 112.5, 27.2, 21.3.
(2ꢀbromophenyl)(mesityl)iodonium trifluoromethanesulfonate (3ag).21 GP2 was used on a 5 mmol scale. Purification by recrystallization
in diethyl ether to afford the product as brown solids (1.54 g, 56%). Mp. 172ꢀ173 °C (Lit. 167ꢀ168 °C)21. 1H NMR (399 MHz, CDCl3) δ
7.74 (dd, J = 8.0, 1.5 Hz, 1H), 7.46 (td, J = 7.7, 1.5 Hz, 1H), 7.33 (ddd, J = 8.9, 7.5, 1.5 Hz, 1H), 7.20 (s, 2H), 6.86 (dd, J = 8.2, 1.4 Hz,
1H), 2.61 (s, 6H), 2.41 (s, 3H). 13C{1H}NMR (100 MHz, CDCl3) δ 145.6, 143.0, 134.6, 133.3, 131.5, 131.2, 131.0, 124.7, 121.6, 120.4 (q,
J = 319.8 Hz), 115.4, 27.2, 21.4.
mesityl(2ꢀ(trifluoromethyl)phenyl)iodonium trifluoromethanesulfonate (3ah).21 GP2 was used on a 5 mmol scale. Purification by
recrystallization in diethyl ether to afford the product as brown solids (891 mg, 33%). Mp. 176ꢀ178 °C (Lit. 180ꢀ181 °C)21. 1H NMR (400
MHz, CDCl3) δ 7.96 – 7.89 (m, 1H), 7.71 (t, J = 7.6 Hz, 1H), 7.54 (td, J = 7.8, 1.6 Hz, 1H), 7.28 (d, J = 8.0 Hz, 1H), 7.19 (s, 2H), 2.62 (s,
6H), 2.41 (s, 3H). 13C{1H}NMR (101 MHz, CDCl3) δ 145.9, 143.1, 135.8, 133.1, 132.2, 131.4, 131.1, 129.6 (d, J = 4.8 Hz), 124.1, 121.9,
120.1 (q, J = 264.9 Hz), 107.5, 27.2, 21.4. 19F NMR (376 MHz, CDCl3) δ ꢀ59.93, ꢀ78.44.
3ꢀ(mesityliodonio)pyridinꢀ1ꢀium bis(trifluoromethanesulfonate) (3ai).2c GP2 was used on a 5 mmol scale. Purification by recrystallization
in diethyl ether to afford the product as light yellow solids (592 mg, 19%). Mp. 155ꢀ158 °C (Lit. 138ꢀ141 °C)2c. 1H NMR (400 MHz, DMSOꢀ
d6) δ 9.06 (d, J = 2.3 Hz, 1H), 8.79 (dd, J = 4.8, 1.3 Hz, 1H), 8.42 (d, J = 8.4 Hz, 1H), 7.55 (dd, J = 8.3, 4.7 Hz, 1H), 7.23 (s, 2H), 2.61 (s,
6H), 2.30 (s, 3H). 13C{1H}NMR (101 MHz, DMSOꢀd6) δ 152.9, 151.9, 143.3, 142.1, 141.6, 129.9, 127.1, 122.6, 120.7 (q, J = 322.4 Hz),
114.2, 26.3, 20.5
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mesityl(4ꢀnitrophenyl)iodonium trifluoromethanesulfonate (3aj).20 GP2 was used on a 5 mmol scale. Purification by recrystallization in
diethyl ether to afford the product as brown solids (827 mg, 32%). Mp. 197ꢀ200 °C (Lit. 208 °C)20 1H NMR (399 MHz, DMSOꢀd6) δ 8.26
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(d, J = 8.4 Hz, 2H), 8.22 – 8.12 (m, 2H), 7.26 (s, 2H), 2.59 (s, 6H), 2.31 (s, 3H). 13C{1H}NMR (100 MHz, DMSOꢀd6) δ 149.3, 143.6, 141.8,
135.5, 130.0, 126.2, 122.8 (q, J = 201.9 Hz), 26.3, 20.6.
oꢀtolyl(pꢀtolyl)iodonium trifluoromethanesulfonate (3ak).11b GP3 was used on a 4 mmol scale. Purification by recrystallization in diethyl
ether to afford the product as brown solids (orthoꢀpara 90%, paraꢀpara 5%, orthoꢀortho 5%, 770 mg, 42%). Mp. 158ꢀ160 °C. 1H NMR
(400 MHz, CDCl3) δ 8.09 (dd, J = 8.1, 1.2 Hz, 1H), 7.85 – 7.71 (m, 2H), 7.52 (td, J = 7.5, 1.2 Hz, 1H), 7.43 (dd, J = 7.7, 1.7 Hz, 1H), 7.22
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