LETTER
Efficient Synthesis of Substituted Polyarylphthalimides
1295
hydroxyimides9 furnish a new type of NHPI analogues
with quite promising catalytic properties.
Lett. 2003, 44, 2053. (f) Shibamoto, A.; Sakaguchi, S.; Ishii,
Y. Tetrahedron Lett. 2002, 43, 8859. (g) Sawatari, N.;
Yokota, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2001, 66,
7889. (h) Wentzel, B. B.; Donners, M. P. J.; Alsters, P. L.;
Feiters, M. C.; Nolte, R. J. M. Tetrahedron 2000, 56, 7797.
(i) Gorgy, K.; Lepretre, J.-C.; Saint-Aman, E.; Einhorn, C.;
Einhorn, J.; Marcadal, C.; Pierre, J.-L. Electrochim. Acta
1998, 44, 385 . For examples of chiral analogues of NHPI,
see: (j) Shen, J.; Tan, C.-H. Org. Biomol. Chem. 2008, 6,
4096. (k) Nechab, M.; Kumar, D. N.; Philouze, C.; Einhorn,
C.; Einhorn, J. Angew. Chem. Int. Ed. 2007, 46, 3080.
(l) Einhorn, C.; Einhorn, J.; Marcadal-Abbadi, C.; Pierre,
J.-L. J. Org. Chem. 1999, 64, 4542.
In conclusion, we have shown that 2-bromomaleimide is
able to replace advantageously maleimide in cycloaddi-
tion reactions involving tetracyclones and acecyclones,
furnishing directly the aromatic imides in high isolated
yields, thus avoiding the use of environment unfriendly
nitrobenzene or of a more time-consuming two-step cy-
cloaddition followed by oxidation procedure. The
straightforward transformation of the new imides so ob-
tained into N-hydroxyimides will give a general access to
two classes of functionally diverse NHPI analogues,
opening the way to new improvements in the domain of
aerobic oxidation organocatalysis.
(3) Nechab, M.; Einhorn, C.; Einhorn, J. Chem. Commun. 2004,
1500.
(4) Sun, Y.; Zhang, W.; Hu, X.; Li, H. J. Phys. Chem. B 2010,
114, 4862.
(5) Ogliaruso, M. A.; Romanelli, M. G.; Becker, E. I. Chem.
Rev. 1965, 65, 261.
(6) For the synthesis of functionalized dibenzylketones and of
the corresponding tetracyclones, see: Potter, R. G.; Hughes,
T. S. J. Org. Chem. 2007, 73, 2995.
Supporting Information for this article is available online at
(7) For recent examples, see: Hapke, M.; Gutnov, A.; Weding,
N.; Anke Spannenberg, A.; Fischer, C.; Benkhäuser-
Schunk, C.; Heller, B. Eur. J. Org. Chem. 2010, 509; and
references cited therein.
(8) Alvarez, L. X.; Bessières, B.; Einhorn, J. Synlett 2008, 1676.
(9) Einhorn, C.; Einhorn, J.; Marcadal-Abbadi, C.; Pierre, J.-L.
Synth. Commun. 2001, 31, 741.
Acknowledgment
Financial support from the CNRS and the Université Joseph Fou-
rier, as well as a fellowship award from the Département de Chimie
Moléculaire (UMR 5250, FR-2607) to R. V., are gratefully acknow-
ledged.
(10) (a) Muranaka, A.; Matsushita, O.; Numao, M.; Kobayashi,
Y.; Kobayashi, N. Tetrahedron Lett. 2008, 49, 1856.
(b) Harris, F. W.; Norris, S. O. J. Heterocycl. Chem. 1972, 9,
1251.
(11) Qiao, X.; Pelczer, I.; Pascal, R. A. Jr. Chirality 1998, 10,
154.
(12) Succinimide has also been evidenced in the reaction mixture
and thus aromatization may be attributed, at least partly, to a
hydrogen transfer from the dihydro intermediate to
maleimide.
(13) A similar strategy has already been reported to obtain
tetraarylphthalic anhydrides from tetracyclones and 2-
chloromaleic anhydride, see: (a) Coan, S. B.; Trucker, D. E.;
Becker, E. I. J. Am. Chem. Soc. 1955, 77, 60. (b) Shapiro,
E. L.; Becker, E. I. J. Am. Chem. Soc. 1953, 75, 4769.
(14) Tedaldi, L. M.; Smith, M. E. B.; Nathani, R. I.; Baker, J. R.
Chem. Commun. 2009, 6583.
References and Notes
(1) (a) Coseri, S. Catal. Rev. 2009, 51, 218. (b) Recupero, F.;
Punta, C. Chem. Rev. 2007, 107, 3800. (c) Ishii, Y.;
Sakaguchi, S. Catal. Today 2006, 117, 105. (d) Sheldon, R.
A.; Arends, I. W. C. E. J. Mol. Catal. A: Chem. 2006, 251,
200. (e) Sheldon, R. A.; Arends, I. W. C. E. Adv. Synth.
Catal. 2004, 346, 1051. (f) Minisci, F.; Recupero, F.;
Pedulli, G. F.; Lucarini, M. J. Mol. Catal. A: Chem. 2003,
204-205, 63. (g) Ishii, Y.; Sakaguchi, S.; Iwahama, T. Adv.
Synth. Catal. 2001, 343, 393.
(2) (a) Shen, J.; Tan, C.-H. Org. Biomol. Chem. 2008, 6, 4096.
(b) Zhang, Q.; Chen, C.; Ma, H.; Miao, H.; Zhang, W.; Sun,
Z.; Xu, J. J. Chem. Technol. Biotechnol. 2008, 83, 1364.
(c) Wang, J.-R.; Liu, L.; Wang, Y.-F.; Zhang, Y.; Deng, W.;
Guo, Q.-X. Tetrahedron Lett. 2005, 46, 4647. (d) Saha, B.;
Koshino, N.; Espenson, J. H. J. Phys. Chem. A 2004, 108,
425. (e) Sawatari, N.; Sakaguchi, S.; Ishii, Y. Tetrahedron
(15) Mukherjee, S.; Corey, E. J. Org. Lett. 2010, 12, 632.
Synlett 2011, No. 9, 1293–1295 © Thieme Stuttgart · New York