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1H), 7.00 (d, J 7.8, 2H), 7.30 (t, J 7.8, 2H), 7.40–7.47 (m, 3H),
8.11–8.15 (m, 3H), 8.37 (d, J 2.1, 1H). dC (CDCl3, 75 MHz)
21.3, 56.4, 104.3, 113.8, 114.3, 116.2, 125.9, 128.5, 130.7,
131.4, 131.5, 134.9, 136.9, 139.1, 139.6, 158.6.
(q, J 3.8), 129.8, 131.4, 134.6 (q, J 33.6), 135.9, 141.6, 143.5,
143.6, 146.1.
3fa/OTs:[16] a colourless solid; mp 163–1658C. nmax
(KBr)/cmꢀ1 2969, 1601, 1568, 1530, 1468, 1350, 1343, 1312,
1300, 1192, 1132, 1043, 1005, 849, 816, 752, 734, 696.
dH (CD3OD, 300 MHz) 2.34 (s, 3H), 2.35 (s, 3H), 2.63
(s, 6H), 6.39 (d, J 7.8, 2H), 7.24 (s, 2H), 7.62 (d, J 7.8, 2H),
8.09 (d, J 7.8, 2H), 8.24 (d, J 7.8, 2H). dC (CD3OD, 75 MHz)
21.1, 21.3, 27.1, 120.0, 122.6, 126.9, 127.5, 129.8, 131.5, 136.3,
141.7, 143.5, 143.7, 146.3, 151.3.
3af/OTs:[15a] a colourless solid; mp 1708C. nmax (KBr)/cmꢀ1
3018, 1585, 1487, 1434, 1265, 1218, 771, 667. dH (CD3OD,
300 MHz) 2.34 (s, 3H), 3.86 (s, 3H), 3.90 (s, 3H), 7.21 (t, J 8.7,
3H), 7.50 (t, J 7.8, 2H), 7.67 (d, J 7.8, 3H), 8.15 (d, J 7.8, 2H),
8.28 (d, J 9.0, 1H), 8.49 (d, J 1.8, 1H). dC (CD3OD, 75 MHz)
21.3, 53.1, 57.1, 104.1, 116.7, 117.1, 124.5, 126.9, 129.8, 133.1,
133.6, 136.2, 139.5, 141.6, 142.0, 143.6, 163.2, 166.0.
3ag/OTs:[16] a colourless solid; mp 183–1858C. nmax
(KBr)/cmꢀ1 3071, 3046, 2934, 1578, 1567, 1482, 1454, 1442,
1402, 1381, 1291, 1235, 1193, 1131, 1043, 1013, 1003, 858,
832, 314, 756, 736, 696. dH (CD3OD, 300 MHz) 2.34 (s, 3H),
5.13 (s, 2H), 7.11 (d, J 8.0, 2H), 7.20 (d, J 8.0, 2H), 7.33–7.41
(m, 5H), 7.50 (t, J 8.0, 2H), 7.67 (t, J 8.0, 3H), 8.05–8.11
(m, 4H). dC (CD3OD, 75 MHz) 21.3, 71.5, 104.7, 116.5, 119.7,
127.0, 128.7, 129.3, 129.6, 129.8, 133.0, 133.5, 136.0, 137.5,
138.5, 141.6, 143.6, 163.5.
3ah/OTs:[15a] a colourless solid; mp 138–1398C. nmax
(KBr)/cmꢀ1 3020, 1568, 1479, 1440, 1217, 1132, 1043, 815,
752, 692. dH (CD3OD, 300 MHz) 2.30 (s, 3H), 6.94–7.02
(m, 4H), 7.16–7.24 (m, 3H), 7.37–7.49 (m, 4H), 7.59–7.70
(m, 3H), 8.08–8.15 (m, 4H). dC (CD3OD, 75 MHz) 21.3,
106.9, 116.5, 121.3, 121.5, 126.3, 126.9, 129.8, 131.4, 133.0,
133.4, 136.2, 138.8, 141.6, 143.6, 156.1, 162.8.
Compound Data for Scheme 4
3aj/OTs:[15b] an off-white solid; mp 1658C. nmax (KBr)/cmꢀ1
3051, 1575, 1469, 1440, 1377, 1191, 1132, 1045, 1014, 991,
815, 746, 680. dH (CD3OD, 300 MHz) 2.33 (s, 3H), 2.49 (s, 3H),
7.03 (d, J 5.1, 1H), 7.19 (d, J 7.2, 2H), 7.46–7.49 (m, 2H), 7.59–
7.67 (m, 3H), 7.83 (d, J 5.1, 1H), 8.05 (d, J 7.8, 2H). dC (CD3OD,
75 MHz) 17.5, 21.3, 98.4, 118.4, 126.9, 129.8, 131.0, 133.0,
133.1, 133.4, 135.4, 137.7, 141.6, 150.0.
3ak/OTs:[15b] a colourless solid; mp 498C. nmax (KBr)/cmꢀ1
3045, 1562, 1469, 1438, 1373, 1330, 1191, 1130, 1043, 1014, 860,
815, 740, 692. dH (CD3OD, 300 MHz) 2.35 (s, 3H), 7.19–7.24
(m, 3H), 7.53 (t, J 7.8, 2H), 7.67 (d, J 7.8, 3H), 7.98 (d, J 5.7, 1H),
8.16 (d, J7.8, 2H). dC (CD3OD, 75 MHz) 21.3, 119.2, 125.6, 126.9,
129.8, 132.1, 133.2, 133.9, 135.9, 139.8, 141.4, 141.7, 143.5.
Acknowledgements
3ai/OTs:[15a] a colourless solid; mp 798C. nmax (KBr)/cmꢀ1
3051, 2981, 1693, 1579, 1487, 1384, 1303, 1191, 1130, 1043,
817, 746, 694. dH (CD3OD, 300 MHz) 2.13 (m, 2H), 2.34
(s, 3H), 2.58 (t, J 8.1, 2H), 3.86 (t, J 6.9, 2H), 7.20 (d, J 7.8,
2H), 7.49 (t, J 7.8, 2H), 7.63–7.69 (m, 3H), 7.80 (d, J 8.7, 2H),
8.13 (d, J 8.7, 4H). dC (CD3OD, 75 MHz) 18.6, 21.3, 35.6, 108.9,
116.5, 123.7, 126.9, 129.8, 133.1, 133.5, 136.2, 137.3, 141.6,
143.6, 144.5, 177.5.
This work was partially supported by a Grant-in-Aid for Scientific Research
(A) from the Japan Society for the Promotion of Science (JSPS), Young
Scientists (B) from the Ministry of Education, Culture, Sports, Science
and Technology (MEXT), and Ritsumeikan Global Innovation Research
Organization (R-GIRO) project. T.D. also acknowledges support from the
Industrial Technology Research Grant Program from the New Energy and
Industrial Technology Development Organization (NEDO) of Japan.
References
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5299. doi:10.1021/CR800332C
Compound Data for Table 2
3ba/OTs:[15a]
a colourless solid; mp 138–1428C. nmax
(b) N. R. Deprez, M. S. Sanford, Inorg. Chem. 2007, 46, 1924.
doi:10.1021/IC0620337
(c) P. J. Stang, J. Org. Chem. 2003, 68, 2997. doi:10.1021/JO030022E
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(e) J. M. C. Frechet, Pure Appl. Chem. 1992, 64, 1239. doi:10.1351/
PAC199264091239
(KBr)/cmꢀ1 3022, 2976, 1454, 1191, 1132, 1045, 985, 732, 694.
dH (CD3OD, 300 MHz) 2.33 (s, 6H), 2.35 (s, 3H), 2.51 (s, 12H),
7.17–7.22 (m, 6H), 7.66 (d, J 7.8, 2H). dC (CD3OD, 75 MHz)
20.8, 21.3, 26.1, 119.1, 126.9, 129.7, 131.7, 141.5, 143.6, 143.6,
145.2.
1
(f) G. F. Koser, in The Chemistry of Functional Groups, Supplement D
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CR010003þ
3ca/OTs: trace amount of formation was confirmed by H
NMR; dH (CD3OD, 300 MHz) 2.31 (s, 3H), 2.33 (s, 3H), 2.63
(s, 6H), 3.79 (s, 3H), 7.00 (d, J 7.8, 2H), 7.15 (s, 2H), 7.17
(d, J 7.8, 2H), 7.64 (d, J 7.8, 2H), 7.83 (d, J 7.8, 2H).
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Top. Curr. Chem.: HypervalentIodine Chemistry-ModernDevelopments
in Organic Synthesis 2003 (Springer: Heidelberg).
3da/OTs: a slightly yellow solid; mp 185–1868C. nmax
(KBr)/cmꢀ1 3040, 2979, 1496, 1467, 1382, 1302, 1191, 1131,
1109, 1085, 1041, 1014, 1001, 850, 815, 695. dH (CD3OD,
400 MHz) 2.34 (s, 3H), 2.35 (s, 3H), 2.62 (s, 6H), 7.19 (d, J 8.8,
2H), 7.20 (s, 2H), 7.48 (d, J 8.8, 2H), 7.63 (d, J 8.8, 2H), 7.86 (d,
J 8.8, 2H). dC (CD3OD, 100.53 MHz) 21.0, 21.3, 27.0, 111.6,
122.6, 126.9, 129.8, 131.3, 133.2, 136.9, 139.8, 141.6, 143.5
(ꢂ 2), 145.9.
(c)V. V. Zhdankin, P.J.Stang, Chem. Rev. 2008, 108, 5299. doi:10.1021/
CR800332C
(d) R. M. Moriarty, O. Prakash, Hypervalent Iodine in Organic
Chemistry: Chemical Transformations 2007 (John Wiley & Sons Ltd:
New York, NY).
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3ea/OTs:[16] a colourless solid; mp 165–1668C. nmax
(KBr)/cmꢀ1 3034, 2969, 2920, 1593, 1449, 1393, 1323, 1300,
1188, 1132, 1103, 1067, 1045, 1015, 1003, 991, 853, 827, 816,
772, 754, 696. dH (CD3OD, 300 MHz) 2.34 (s, 3H ꢂ 2), 2.63
(s, 6H), 7.18 (d, J 7.8, 2H), 7.22 (s, 2H), 7.62 (d, J 7.8, 2H),
7.76 (d, J 7.8, 2H), 8.06 (d, J 7.8, 2H). dC (CD3OD, 75 MHz)
21.1, 21.3, 27.1, 118.1, 122.5, 124.7 (q, J 271), 126.9, 129.7