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Org. Lett., 2012, 14, 3020; (f) U. Farid and T. Wirth, Angew. 16 W. Breuer and H. J. Frohn, J. Fluorine Chem., 1987, 34, 443.
Chem., Int. Ed., 2012, 51, 3462; (g) N. O. Ilchenko, 17 I. A. Mironova, P. S. Postnikov, R. Y. Yusubova,
M. Hedberg and K. J. Szabo, Chem. Sci., 2017, 8, 1056; (h)
Y. Tamura, T. Yakura, Y. Shirouchi and J. Haruta, Chem.
A. Yoshimura, T. Wirth, V. V. Zhdankin, V. N. Nemykin
and M. S. Yusubov, Beilstein J. Org. Chem., 2018, 14, 1854.
Pharm. Bull., 1986, 34, 1061; (i) M. W. Justik, in PATAI'S 18 T. Birchall, R. D. Myers, H. D. Waard and G. J. Schrobilgen,
Chemistry of Functional Groups [online], John Wiley & Sons,
Ltd, New York, 2009, pp. 1–88.
2 (a) J. D. Haupt, M. Berger and S. R. Waldvogel, Org. Lett.,
Inorg. Chem., 1982, 21, 1068.
19 A. R. Katritzky, J. K. Gallos and H. D. Durst, Magn. Reson.
Chem., 1989, 27, 815.
2019, 21, 242; (b) L. Wang, H. Li and L. Wang, Org. Lett., 20 F. M. Beringer and P. Bodlaender, J. Org. Chem., 1968, 33,
2018, 20, 1663; (c) S. R. Kandimalla, S. P. Parvathaneni, 2981.
G. Sabitha and B. V. S. Reddy, Eur. J. Org. Chem., 2019, 21 N. S. Zerov, V. V. Zhdankin, V. V. Dan'kov and
1687; (d) I. Colomer, C. Batchelor-McAuley, B. Odell, A. S. Koz'min, J. Org. Chem. USSR, 1984, 20, 401.
T. J. Donohoe and R. G. Compton, J. Am. Chem. Soc., 2016, 22 (a) D. H. R. Barton and D. Crich, Tetrahedron, 1985, 41, 4359;
138, 8855; (e) D. Bhattacherjee, S. Ram, A. S. Chauhan,
Yamini, Sheetal and P. Das, Chem.–Eur. J., 2019, 25, 5934.
3 (a) J. Kalim, T. Duhail, T.-N. Le, N. Vanthuyne, E. Anselmi,
(b) R. Gleiter and G. Mueller, J. Org. Chem., 1988, 53, 3912; (c)
T. Iida, S. Nishida, F. C. Chang, T. Niwa, J. Goto and
T. Nambara, Chem. Pharm. Bull., 1993, 41, 763.
¨
A. Togni and E. Magnier, Chem. Sci., 2019, 10, 10516; (b) 23 H. Kunzer, G. Sauer and R. Wiechert, Tetrahedron, 1989, 45,
G.-X. Li, C. A. Morales-Rivera, F. Gao, Y. Wang, G. He, 6409.
P. Liu and G. Chen, Chem. Sci., 2017, 8, 7180; (c) J. Qurban, 24 (a) N. Soldatova, P. Postnikov, A. A. Troyan, A. Yoshimura,
M. Elsherbini, H. Alharbia and T. Wirth, Chem. Commun.,
2019, 55, 7998; (d) A. Yoshimura, M. T. Shea,
C. L. Makitalo, M. E. Jarvi, G. T. Rohde, A. Saito,
M. S. Yusubov and V. V. Zhdankin, Beilstein J. Org. Chem.,
2018, 14, 1016; (e) Y. Wang, H. Yuan, H. Lu and
W.-H. Zheng, Org. Lett., 2018, 20, 2555.
4 Z. Begum, G. Bhavani, B. Sridhar and B. V. S. Reddy,
Synthesis, 2018, 50, 4089.
5 P. Ajda, J. Markus, S. Stojan, Z. Marko, I. Jernej and
J. A. Gladysz, J. Org. Chem., 2009, 74, 3133.
M. S. Yusubov and V. V. Zhdankin, Tetrahedron Lett., 2016,
57, 4254; (b) J. G. Sharein and H. Saltzman, Org. Synth.,
1963, 43, 65; (c) R. I. Davidson and P. J. Kropp, J. Org.
Chem., 1982, 47, 1904; (d) N. Taneja and R. K. Peddinti,
Tetrahedron Lett., 2016, 57, 3958; (e) A. Bravo, F. Fontana,
G. Fronza, F. Minisci and A. Serri, Tetrahedron Lett., 1995,
36, 6945; (f) A. Watanabe, K. Miyamoto, T. Okada, T. Asawa
and M. Uchiyama, J. Org. Chem., 2018, 83, 14262; (g)
M. S. Yusubov, A. A. Zagulyaeva and V. V. Zhdankin,
Chem.–Eur. J., 2009, 15, 11091.
6 J. Hu, B. Xing and C. Ni, Angew. Chem., Int. Ed., 2018, 57, 25 (a) R. Bell and K. J. Morgan, J. Chem. Soc., 1960, 1960, 1209;
9896.
(b) M. S. Yusubov, K. W. Chi, J. Y. Park, R. Karimov and
V. V. Zhdankin, Tetrahedron Lett., 2006, 47, 6305; (c)
A. A. Mironova, V. V. Orda, L. M. Yagupolskii and
I. I. Maletina, Synthesis, 1983, 1983, 456; (d)
L. Troiangautier, J. D. Winter, P. Gerbaux and
C. Moucheron, J. Org. Chem., 2013, 78, 11096.
7 J. L. Dektar and N. P. Hacker, J. Org. Chem., 1990, 55, 639.
8 (a) S. Kyrill, K. Raffael and T. Antonio, J. Org. Chem., 2010, 40,
7678; (b) S. Kawamura, D. Sekine and M. Sodeoka, J. Fluorine
Chem., 2017, 203, 115; (c) E. Patrick, G. Sebastian and
T. Antonio, Chem.–Eur. J., 2010, 12, 2579.
9 (a) J. Gallos, A. Varvoglis and N. W. Alcock, J. Chem. Soc., 26 A. Maity, S.-M. Hyun, A. K. Wortman and D. C. Powers,
Perkin Trans. 1, 1985, 1985, 757; (b) T. Dohi, T. Uchiyama, Angew. Chem., Int. Ed., 2018, 57, 7205.
D. Yamashita, N. Washimi and Y. Kita, Tetrahedron Lett., 27 (a) Compound tends to decompose into o-
nitroiodobenzene if stored in air at room temperature. It is
necessary to have compound stored under N2
1
2011, 52, 2212.
10 P. J. Stang, B. L. Williamson and V. V. Zhdankin, J. Am. Chem.
Soc., 1991, 113, 5870.
11 Y.-D. Yang, A. Azuma, E. Tokunaga, M. Yamasaki and
N. Shibata, J. Am. Chem. Soc., 2014, 44, 8782.
12 (a) S. V. Kohlhepp and T. Gulder, Chem. Soc. Rev., 2016, 45,
6270; (b) T. Hokamp, L. Mollari, L. C. Wilkins, R. L. Melen
and T. Wirth, Angew. Chem., Int. Ed., 2018, 57, 8306; (c)
M. Bedin, A. Karim, M. Reitti, A. C. C. Carlsson, F. Topic,
M. Cetina, F. F. Pan, V. Havel, F. Al-Ameri, V. Sindelar,
1
a
atmosphere and at lower temperature (<3 ꢀC); (b) It is
worth noting that compound 1 is relatively stable in
MeOH, as the use of MeOH/CH2Cl2 for column
purication does not bring about any obvious
decomposition. We tried to dissolve compound 1 in
ethanol,
p-methoxybenzyl
alcohol,
and
p-
chlorophenylethanol. However, the poor solubility of 1
allowed it to be well stored in these alcoholic solvents at
room temperature for more than one day. However, an
´
K. Rissanen, J. Grafenstein and M. Erdelyi, Chem. Sci.,
2015, 6, 3746; (d) W. C. Agosta, Tetrahedron Lett., 1965, 6,
2681.
13 P. J. Stevenson, A. B. Treacy and M. Nieuwenhuyzen, J. Chem.
Soc., Perkin Trans. 2, 1997, 589.
obvious decomposition of compound
1
into o-
nitroiodobenzene was observed if it was dissolved in
benzyl alcohol and stirred for 10 minutes at room
temperature.
14 D. B. Dess and J. C. Martin, J. Org. Chem., 1983, 15, 4155.
15 S. Hara, M. Monoi, R. Umemura and C. Fuse, Tetrahedron,
2012, 68, 10145.
28 M. S. Yusubov, D. Y. Svitich, A. Yoshimura, V. N. Nemykin
and V. V. Zhdankin, Chem. Commun., 2013, 49, 11269.
Chem. Sci.
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