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SPECIAL TOPIC
(h) Derikvand, F.; Bigi, F.; Maggi, R.; Piscopo, C. G.;
Sartori, G. J. Catal. 2010, 271, 99. (i) Romanelli, G. P.;
Villabrille, P. I.; Vazquez, P. G.; Caceres, C. V.; Tundo, P.
Lett. Org. Chem. 2008, 5, 332. (j) Bernini, R.; Mincione, E.;
Barantini, M.; Fabrizi, G.; Pasqualetti, M.; Tempesta, S.
Tetrahedron 2006, 62, 7733. (k) Zalomaeva, O. V.; Sorokin,
A. B. New J. Chem. 2006, 30, 1768. (l) Iwasa, S.;
Fakhruddin, A.; Widagdo, H. S.; Nishiyama, H. Adv. Synth.
Catal. 2005, 347, 517. (m) Kim, S.; Kim, D.; Park, J. Adv.
Synth. Catal. 2009, 351, 2573. (n) Miyamura, H.; Shiramizu,
M.; Matsubara, R.; Kobayashi, S. Angew. Chem. Int. Ed.
2008, 47, 8093. (o) Oelgemoller, M.; Healy, N.; de Oliveira,
L.; Jung, C.; Mattay, J. Green Chem. 2006, 8, 831.
2-Methoxy-1,4-benzoquinone (3v);6b Conversion in Water in
the Presence of Methanol Additive (Scheme 3, Equation 4)
To a stirred soln of the μ-oxo oxidant 1 (71.6 mg, 0.22 × 0.5 mmol,
0.55 equiv) in H2O (1 mL) containing a small amount of MeOH
(2.5%), phenyl ether 2v (33.6 mg, 0.20 mmol) was added in one
portion at 0 °C. After stirring for 2 h at this temperature, extraction
of the oily float with a small amount of toluene followed by column
chromatography (silica gel, hexane–EtOAc) gave pure quinone 3v
(24.9 mg, 0.18 mmol, 90%) as a yellow solid; mp 140–142 °C.
IR (KBr): 3290 (w), 3070 (m), 2986 (m), 2951 (m), 2853 (m), 2328
(w), 2255 (w), 1676 (s), 1650 (s), 1622 (s), 1596 (s), 1512 (w), 1456
(m), 1360 (s), 1312 (s), 1247 (s), 1183 (m), 1115 (s), 987 (s), 910
(s), 863 (s), 799 (m), 761 (s), 641 cm–1 (m).
1H NMR (400 MHz, CDCl3): δ = 3.82 (s, 3 H), 5.96 (s, 1 H), 6.65–
6.75 (m, 2 H).
13C NMR (100 MHz, CDCl3): δ = 56.2, 107.7, 134.4, 137.2, 158.6,
181.7, 187.4.
(5) (a) Moriarty, R. M.; Prakash, O. Org. React. 2001, 57, 327.
(b) Barret, R.; Daudon, M. Tetrahedron Lett. 1990, 31,
4871. (c) Lebrasseur, N.; Fan, G.-J.; Oxoby, M.; Looney, M.
A.; Quideau, S. Tetrahedron 2005, 61, 1551. (d) Ficht, S.;
Mulbaier, M.; Giannis, A. Tetrahedron 2001, 57, 4863.
(e) Pelter, A.; Elgendy, S. Tetrahedron Lett. 1988, 29, 677.
(f) Ley, S. V.; Thomas, A. W.; Finch, H. J. Chem. Soc.,
Perkin Trans. 1 1999, 669. (g) Rocaboy, C.; Gladysz, J. A.
Chem.–Eur. J. 2003, 9, 88. (h) Tesevic, V.; Gladysz, J. A.
Green Chem. 2005, 7, 833. (i) Wu, A.; Duan, Y.; Xu, D.;
Penning, T. M.; Harvey, R. G. Tetrahedron 2010, 66, 2111.
For recent reviews, see: (j) Ciufolini, M. A.; Braun, N. A.;
Canesi, S.; Ousmer, M.; Chang, J.; Chai, D. Synthesis 2007,
3759. (k) Quideau, S.; Pouységu, L.; Deffieux, D. Synlett
2008, 467. (l) Pouységu, L.; Deffieux, D.; Quideau, S.
Tetrahedron 2010, 66, 2235.
Acknowledgement
This work was partially supported by a Grant-in-Aid for Scientific
Research (A) from JSPS, a Grant-in-Aid for Scientific Research on
Innovative Areas ‘Advanced Molecular Transformations by Orga-
nocatalysts’ from MEXT, and Ritsumeikan Global Innovation Re-
search Organization (R-GIRO) project. T.D. also acknowledges
financial support from the Asahi Glass Foundation and the Industri-
al Technology Research Grant Program from the NEDO of Japan.
(6) (a) Tamura, Y.; Yakura, T.; Haruta, J.; Kita, Y. J. Org.
Chem. 1987, 52, 3927. (b) Tamura, Y.; Yakura, T.; Tohma,
H.; Kikuchi, K.; Kita, Y. Synthesis 1989, 126. (c) Kita, Y.;
Yakura, T.; Tohma, H.; Kikuchi, K.; Tamura, Y.
References
(1) (a) The Chemistry of Quinonoid Compounds, Part 2; Patai,
S., Ed.; Wiley: New York, 1988. (b) Naturally Occurring
Quinones IV Recent Advances; Thomson, R. H., Ed.;
Blackie Academic & Professional: London, 1997.
Tetrahedron Lett. 1989, 30, 1119. (d) Kita, Y.; Tohma, H.;
Kikuchi, K.; Inagaki, M.; Yakura, T. J. Org. Chem. 1991, 56,
435. For a review, see: (e) Tohma, H.; Kita, Y. Top. Curr.
Chem. 2003, 224, 209. Applications of phenolic oxidations
in our laboratory: (f) Kita, Y.; Tohma, H.; Inagaki, M.;
Hatanaka, K.; Yakura, T. J. Am. Chem. Soc. 1992, 114,
2175. (g) Kita, Y.; Takada, T.; Gyoten, M.; Tohma, H.;
Zenk, M. H.; Eichhorn, J. J. Org. Chem. 1996, 61, 5857.
(h) Kita, Y.; Egi, M.; Takada, T.; Tohma, H. Synthesis 1999,
885. (i) Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.;
Hamada, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63,
6625. (j) Kita, Y.; Egi, M.; Tohma, H. Chem. Commun.
1999, 143. (k) Tohma, H.; Harayama, Y.; Hashizume, M.;
Iwata, M.; Kiyono, Y.; Egi, M.; Kita, Y. J. Am. Chem. Soc.
2003, 125, 11235. (l) Hamamoto, H.; Shiozaki, Y.; Nambu,
H.; Hata, K.; Tohma, H.; Kita, Y. Chem.–Eur. J. 2004, 10,
4977. (m) Wada, Y.; Otani, K.; Endo, N.; Harayama, Y.;
Kamimura, D.; Yoshida, M.; Fujioka, H.; Kita, Y. Org. Lett.
2009, 11, 4048. For recent investigations, see: (n) Dohi, T.;
Maruyama, A.; Yoshimura, M.; Morimoto, K.; Tohma, H.;
Kita, Y. Angew. Chem. Int. Ed. 2005, 44, 6193. (o) Dohi, T.;
Maruyama, A.; Minamitsuji, Y.; Takenaga, N.; Kita, Y.
Chem. Commun. 2007, 1224. (p) Dohi, T.; Minamitsuji, Y.;
Maruyama, A.; Hirose, S.; Kita, Y. Org. Lett. 2008, 10,
3559. (q) Minamitsuji, Y.; Kato, D.; Fujioka, H.; Dohi, T.;
Kita, Y. Aust. J. Chem. 2009, 62, 648. (r) Dohi, T.;
(c) Quideau, S.; Pouysegu, L. Org. Prep. Proced. Int. 1999,
31, 617. (d) Scott, J. D.; Williams, R. M. Chem. Rev. 2002,
102, 1669. (e) Decker, H.; Schweikardt, T.; Tuczek, F.
Angew. Chem. Int. Ed. 2006, 45, 4546. (f) Bayen, S.;
Barooah, N.; Sharma, R. J.; Sen, T. K.; Karmakar, A.;
Baruah, J. B. Dyes Pigm. 2007, 75, 770. (g) Dunlap, T.;
Chandrasena, R. E. P.; Wang, X.; Sinha, V.; Wang, Z.;
Thatcher, G. R. J. Chem. Res. Toxicol. 2007, 20, 1903.
(h) Klan, P.; Wirz, J. Photochemistry of Organic
Compounds: From Concepts to Practice; Wiley: New York,
2009, see also refs. 3 and 4.
(2) Our SciFinder® search detected more than ten thousand hits
of references dealing with quinone structures in the years of
2010 and 2011, respectively.
(3) (a) Dudfield, P. J. In Comprehensive Organic Synthesis,
Vol. 7; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford,
1991, 345. (b) Gallagher, P. T. Contemp. Org. Synth. 1996,
3, 433. (c) Akai, S.; Kita, Y. Org. Prep. Proced. Int. 1998,
30, 603. (d) Owton, W. M. J. Chem. Soc., Perkin Trans. 1
1999, 2409. (e) Abraham, I.; Joshi, R.; Pardasani, P.;
Pardasani, R. T. J. Braz. Chem. Soc. 2011, 22, 385.
(4) For examples of recently reported methods, see: (a) Ali, M.
H.; Niedbalski, M.; Bohnert, G.; Bryant, D. Synth. Commun.
2006, 36, 1751. (b) Suante, H.; Mahanti, M. K. Oxid.
Commun. 2006, 29, 266. (c) Tajbakhsh, M.; Hosseinzadeh,
R.; Sadatshahabi, M. Synth. Commun. 2005, 35, 1547.
(d) Hashemi, M. M.; Akhbari, M. Russ. J. Org. Chem. 2005,
41, 935. (e) Lee, C. W.; Jin, S. H.; Yoon, K. S.; Jeong, H. M.;
Chi, K. Tetrahedron Lett. 2009, 50, 559. (f) Tajbakhsh, M.;
Lakouraj, M. M.; Ramzanian-Lehmali, F. Synlett 2006,
1724. (g) Moeller, K.; Wienhoefer, G.; Schroeder, K.; Join,
B.; Junge, K.; Beller, M. Chem.–Eur. J. 2010, 16, 10300.
Yamaoka, N.; Kita, Y. Tetrahedron 2010, 66, 5775.
(7) For recent reviews and publications, see: (a) Hypervalent
Iodine Chemistry: Modern Developments in Organic
Synthesis, In Topics in Current Chemistry, Wirth, T., Ed.;
Springer Verlag: Berlin, 2003. (b) Wirth, T. Angew. Chem.
Int. Ed. 2005, 44, 3656. (c) Zhdankin, V. V.; Stang, P. J.
Chem. Rev. 2008, 108, 5299. (d) Dohi, T.; Ito, M.; Yamaoka,
N.; Morimoto, K.; Fujioka, H.; Kita, Y. Tetrahedron 2009,
Synthesis 2012, 44, 1183–1189
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