Minkin, Chem. Rev., 2004, 104, 2751; (e) R. Pudzich, T. Fuhrmann-
Lieker and J. Salbeck, Adv. Polym. Sci., 2006, 199, 83; (f) T. P. I. Saragi,
T. Spehr, A. Siebert, T. Fuhrmann-Lieker and J. Salbeck, Chem. Rev.,
2007, 107, 1011; (g) K. Ding, Z. Han and Z. Wang, Chem.–Asian J.,
2009, 4, 32.
2 The updated synthetic reviews: (a) S. Kotha, A. C. Deb, K. Lahiri and
E. Manivannan, Synthesis, 2009, 165; (b) S. Rosenberg and R. Leino,
Synthesis, 2009, 2651; (c) S. Rodriguez and P. Wipf, Synthesis, 2004,
2767; (d) C. Cismas, A. Terec, S. Mager and I. Grosu, Curr. Org. Chem.,
2005, 9, 1287.
3 For the studies in our laboratory using hypervalent iodine reagents, see
the selected examples: (a) Y. Tamura, T. Yakura, J. Haruta and Y. Kita,
J. Org. Chem., 1987, 52, 3927; (b) Y. Kita, H. Tohma, M. Inagaki, K.
Hatanaka and T. Yakura, J. Am. Chem. Soc., 1992, 114, 2175; (c) Y.
Kita, T. Takada, M. Gyoten, H. Tohma, M. H. Zenk and J. Eichhorn,
J. Org. Chem., 1996, 61, 5857; (d) M. Arisawa, N. G. Ramesh, M.
Nakajima, H. Tohma and Y. Kita, J. Org. Chem., 2001, 66, 59; (e) H.
Tohma and Y. Kita, Top. Curr. Chem., 2003, 224, 209 and references
cited therein.
4 (a) T. R. Appel, N. A. M. Yehia, U. Baumeister, H. Hartung, R. Kluge,
D. Stro¨hl and E. Fangha¨nel, Eur. J. Org. Chem., 2003, 47; (b) X. Zhang
and R. C. Larock, J. Am. Chem. Soc., 2005, 127, 12230; (c) B.-X. Tang,
D.-J. Tang, S. Tang, Q.-F. Yu, Y.-H. Zhang, Y. Liang, P. Zhong and
J.-H. Li, Org. Lett., 2008, 10, 1063; (d) B. X. Tang, Q. Yin, R. Y. Tang
and J. H. Li, J. Org. Chem., 2008, 73, 9008 and references therein.
5 (a) T. Dohi, A. Maruyama, M. Yoshimura, K. Morimoto, H. Tohma
and Y. Kita, Angew. Chem., Int. Ed., 2005, 44, 6193; (b) M. Ochiai, Y.
Takeuchi, T. Katayama, T. Sueda and K. Miyamato, J. Am. Chem. Soc.,
2005, 127, 12244; (c) R. D. Richardson and T. Wirth, Angew. Chem.,
Int. Ed., 2006, 45, 4402; (d) E. A. Merritt, V. M. T. Carneiro, L. F. Jr.
Silva and B. Olofsson, J. Org. Chem., 2010, 75, 7416.
8 Very recently, we reported the isolation of new iodonium salts formed
by the spirocyclization, in which the possibility of a similar one-
pot synthesis was described for specific cases. The utilization and
optimization of the in situ generated hypervalent iodine species from
iodoarenes were not treated in that study. See: T. Dohi, D. Kato, R.
Hyodo, D. Yamashita, M. Shiro and Y. Kita, Angew. Chem., Int. Ed.,
2011, 50, 3784.
9 The bis(iodoarene)s also showed the high catalytic efficiencies in the
spirocyclization of the N-methoxy aryl amides. See: T. Dohi, N.
Takenaga, K.-I. Fukushima, T. Uchiyama, D. Kato, M. Shiro, H.
Fujioka and Y. Kita, Chem. Commun., 2010, 46, 7697.
10 Other regioisomeric bis(iodoarene)s of 3h were less effective than the
2,2¢-derivative in this transformation.
11 The fluoroalcohols can accelerate generation of hypervalent iodine(III)
species from iodoarenes and formation of the diaryliodonium salts.
See: (a) T. Dohi, A. Maruyama, Y. Minamitsuji, N. Takenaga and Y.
Kita, Chem. Commun., 2007, 1224; (b) T. Dohi, M. Ito, K. Morimoto,
Y. Minamitsuji, N. Takenaga and Y. Kita, Chem. Commun., 2007,
4152; (c) T. Dohi, N. Yamaoka and Y. Kita, Tetrahedron, 2010, 66,
5775.
12 The use of excess amounts of the nucleophiles (~5 equiv.) was possible in
order to avoid introduction of mCPBA to the final spirocyclic products,
though it was a very minor competitive path.
13 For selected examples of natural product syntheses containing the
related ortho-spirolactone structures, see: (a) K. Watanabe, Y. Iwata,
S. Adachi, T. Nishikawa, Y. Yoshida, S. Kameda, M. Ide, Y. Saikawa
and M. Nakata, J. Org. Chem., 2010, 75, 5573; (b) D. A. Henderson, P.
N. Collier, G. Pave, P. Rzepa, A. J. P. White, J. N. Burrows and A. G.
M. Barrett, J. Org. Chem., 2006, 71, 2434; (c) F. Konno, T. Ishikawa,
M. Kawahata and K. Yamaguchi, J. Org. Chem., 2006, 71, 9818; (d) C.
Cox and S. J. Danishefsky, Org. Lett., 2000, 2, 3493.
6 Formation of alkenylodonium salts by the oxygenations of alkynes:
(a) G. F. Koser, L. Rebrovic and R. H. Wettach, J. Org. Chem., 1981,
46, 4324; (b) L. Rebrovic and G. F. Koser, J. Org. Chem., 1984, 49, 4700;
(c) T. Kitamura, R. Furuki, H. Taniguchi and P. J. Stang, Tetrahedron
Lett., 1990, 31, 703. On the other hand, no general method using
hypervalent iodine reagent to furnish carbon–carbon bonds toward
alkynes was reported.
14 The pKa values of conjugated acids of the nucleophiles are typically
lower than 5.
15 Comparable reaction yields were obtained for the substrates 1 in Table
1 in these nucleophiles.
16 (a) M. Ochiai, K. Oshima and Y. Masaki, Chem. Lett., 1994, 871; (b) M.
Ochiai, T. Shu, T. Nagaoka and Y. Kitagawa, J. Org. Chem., 1997, 62,
2130.
7 Reactions of alkenyliodonium salts with nucleophiles: (a) M. Ochiai, K.
Sumi, Y. Takaoka, M. Kunishima, Y. Nagao, M. Shiro and E. Fujita,
Tetrahedron, 1988, 44, 4095; (b) J.-M. Chen and X. Huang, Synlett,
2004, 552; (c) J. Yan, H. Jin and Z. Chen, J. Chem. Res., 2007, 233.
17 For the related bis(iodoarene) catalysts developed by us, see: (a) T.
Dohi, A. Maruyama, N. Takenaga, K. Senami, Y. Minamitsuji, H.
Fujioka, S. Caemmerer and Y. Kita, Angew. Chem., Int. Ed., 2008, 47,
3787; (b) T. Dohi and Y. Kita, Chem. Commun., 2009, 2073.
6902 | Org. Biomol. Chem., 2011, 9, 6899–6902
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