FEATURE ARTICLE
Brominations with Pr4NBr9
747
(3) (a) Buckles, R. E.; Popov, A. I.; Zelezny, W. F.; Smith, R. J.
J. Am. Chem. Soc. 1951, 73, 4525. (b) Buckles, R. E.; Harris,
L. J. Am. Chem. Soc. 1957, 79, 886.
Z. Naturforsch. 2013, 68b, 1103. (k) Haller, H.; Ellwanger,
M.; Higelin, A.; Riedel, S. Z. Anorg. Allg. Chem. 2012, 638,
553.
(4) (a) Trowbridge, P. F.; Diehl, O. C. J. Am. Chem. Soc. 1897,
19, 558. (b) Djerassi, C.; Scholz, C. R. J. Am. Chem. Soc.
1948, 70, 417. (c) Merker, P. C.; Vona, J. A. J. Chem. Educ.
1949, 26, 613.
(5) (a) Chiappe, C.; Capraro, D.; Conte, V.; Pieraccini, D. Org.
Lett. 2001, 3, 1061. (b) Chiappe, C.; Leandri, E.; Pieraccini,
D. Chem. Commun. 2004, 2536. (c) Salazar, J.; Dorta, R.
Synlett 2004, 1318. (d) Kavala, V.; Naik, S.; Patel, B. K.
J. Org. Chem. 2005, 70, 4267. (e) Borikar, S. P.; Daniel, T.;
Paul, V. Tetrahedron Lett. 2009, 50, 1007.
(15) (a) Bellucci, G.; Bianchini, R.; Ambrosetti, R.; Ingrosso, G.
J. Org. Chem. 1985, 50, 3313. (b) Bellucci, G.; Bianchini,
R.; Vecchiani, S. J. Org. Chem. 1986, 51, 4224. (c) Bellucci,
G.; Chiappe, C.; Moro, G. L. J. Org. Chem. 1997, 62, 3176.
(16) Ruasse, M.-F.; Motallebi, S.; Galland, B. J. Am. Chem. Soc.
1991, 113, 3440.
(17) See the Supporting Information.
(18) Put, J.; Maes, G.; Huyskens, P.; Zeegers-Huyskens, T.
Spectrochim. Acta 1981, 37A, 699.
(19) Trace amounts of Br2 originating from the small excess of
Br2 used in the preparation became visible upon dissolving
the material in CH2Cl2. However, this was removed by
crystallization and the resulting nonabromide material
showed identical bromination performance.
(20) Pincock, J. A.; Yates, K. Can. J. Chem. 1970, 48, 3332.
(21) Weber, F. G. Tetrahedron 1969, 25, 4283.
(22) Berthelot, J.; Benammar, Y.; Lange, C. Tetrahedron Lett.
1991, 32, 4135.
(6) Djerassi, C. Chem. Rev. 1948, 43, 271.
(7) (a) Eguchi, H.; Kawaguchi, H.; Yoshinaga, S.; Nishida, A.;
Nishiguchi, T.; Fujisaki, S. Bull. Chem. Soc. Jpn. 1994, 67,
1918. (b) Chassaing, C.; Haudrechy, A.; Langlois, Y.
Tetrahedron Lett. 1997, 38, 4415.
(8) Magen, S.; Oren, J.; Fuchs, B. Tetrahedron Lett. 1984, 25,
3369.
(9) (a) Omura, K. J. Org. Chem. 1996, 61, 2006. (b) Bertelsen,
S.; Halland, N.; Bachmann, S.; Marigo, M.; Braunton, A.;
Jørgensen, K. A. Chem. Commun. 2005, 4821.
(23) Tanaka, K.; Shiraishi, R.; Toda, F. J. Chem. Soc., Perkin
Trans. 1 1999, 3069.
(10) For example, see: (a) Barhate, N. B.; Gajare, A. S.;
Wakharkar, R. D.; Bedekar, A. V. Tetrahedron 1999, 55,
11127. (b) Kim, E.-H.; Koo, B.-S.; Song, C.-E.; Lee, K.-J.
Synth. Commun. 2001, 31, 3627. (c) Nair, V.; Panicker, S.
B.; Augustine, A.; George, T. G.; Thomas, S.; Vairamani, M.
Tetrahedron 2001, 57, 7417. (d) Narender, N.; Mohan, K. V.
V. K.; Kulkarni, S. J.; Raghavan, K. V. J. Chem. Res. 2003,
597. (e) Zhang, G.; Liu, R.; Xu, Q.; Ma, L.; Liang, X. Adv.
Synth. Catal. 2006, 348, 862. (f) Terent’ev, A. O.;
Khodykin, S. V.; Krylov, I. B.; Ogibin, Y. N.; Nikishin, G.
I. Synthesis 2006, 1087. (g) Tajik, H.; Mohammadpoor-
Baltork, I.; Albadi, J. Synth. Commun. 2007, 37, 323.
(h) Das, B.; Srinivas, Y.; Sudhakar, C.; Damodar, K.;
Narender, R. Synth. Commun. 2008, 39, 220.
(i) Firouzabadi, H.; Iranpoor, N.; Kazemi, S. Can. J. Chem.
2009, 87, 1675. (j) Kumar, M. A.; Rohitha, C. N.; Kulkarni,
S. J.; Narender, N. Synthesis 2010, 1629. (k) Macharla, A.
K.; Nappunni, R. C.; Marri, M. R.; Peraka, S.; Nama, N.
Tetrahedron Lett. 2012, 53, 191. (l) Yousefi-Seyf, J.;
Tajeian, K.; Kolvari, E.; Koukabi, N.; Khazaei, A.; Zolfigol,
M. A. Bull. Korean Chem. Soc. 2012, 33, 2619. (m) Prebil,
R.; Laali, K. K.; Stavber, S. Org. Lett. 2013, 15, 2108.
(11) Haller, H.; Ellwanger, M.; Higelin, A.; Riedel, S. Angew.
Chem. Int. Ed. 2011, 50, 11528.
(24) Ma, X.; Li, W.; Li, X.; Tao, X.; Fan, W.; Xie, X.; Ayad, T.;
Ratovelomanana-Vidal, V.; Zhang, Z. Chem. Commun.
2012, 48, 5352.
(25) Zysman-Colman, E.; Arias, K.; Siegel, J. S. Can. J. Chem.
2009, 87, 440.
(26) Chhattise, P. K.; Ramaswamy, A. V.; Waghmode, S. B.
Tetrahedron Lett. 2008, 49, 189.
(27) Oberhauser, T. J. Org. Chem. 1997, 62, 4504.
(28) Kikushima, K.; Moriuchi, T.; Hirao, T. Tetrahedron Lett.
2010, 51, 340.
(29) Liu, J.; Li, W.; Wang, C.; Li, Y.; Li, Z. Tetrahedron Lett.
2011, 52, 4320.
(30) Ye, C.; Shreeve, J. M. J. Org. Chem. 2004, 69, 8561.
(31) (a) Choi, H. Y.; Chi, D. Y. Org. Lett. 2003, 5, 411. (b) See
also supporting information in: Streuff, J.; Feurer, M.;
Bichovski, P.; Frey, G.; Gellrich, U. Angew. Chem. Int. Ed.
2012, 51, 8661.
(32) Malanga, C.; Mannucci, S.; Lardicci, L. Tetrahedron 1998,
54, 1021.
(33) Hanson, K.; Roskop, L.; Djurovich, P. I.; Zahariev, F.;
Gordon, M. S.; Thompson, M. E. J. Am. Chem. Soc. 2010,
132, 16247.
(34) Li, B.; Gao, L.; Bian, F.; Yu, W. Tetrahedron Lett. 2013, 54,
1063.
(12) Chattaway, F. D.; Hoyle, G. J. Chem. Soc., Trans. 1923, 123,
654.
(35) Pahari, P.; Rohr, J. J. Org. Chem. 2009, 74, 2750.
(36) Graczyk, P. P.; Dimopoulos, P.; Bhatia, P. G.; Farthing, C.
N.; Khan, A. WO 2008,095,944, 2008.
(37) Dirac, P. A. M. Proc. R. Soc. London, Ser. A 1929, 123, 714.
(38) Slater, J. C. Phys. Rev. 1951, 81, 385.
(39) Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58,
1200.
(40) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
(41) Perdew, J. P. Phys. Rev. B 1986, 33, 8822.
(42) Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7,
3297.
(43) Grimme, S. J. Chem. Phys. 2003, 118, 9095.
(44) Turbomole 6.3 ed., a development of University of
Karlsruhe and Forschungszentrum Karlsruhe GmbH,
(45) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys.
1985, 83, 735.
(13) Farkas, L.; Schächter, O. J. Am. Chem. Soc. 1949, 71, 2252.
(14) (a) Strømme, K. O. Acta Chem. Scand. 1959, 13, 2089.
(b) Kalina, D. W.; Lyding, J. W.; Ratajack, M. T.;
Kannewurf, C. R.; Marks, T. J. J. Am. Chem. Soc. 1980, 102,
7854. (c) Cunningham, C. W.; Burns, G. R.; McKee, V.
Inorg. Chim. Acta 1990, 167, 135. (d) Robertson, K. N.;
Bakshi, P. K.; Cameron, T. S.; Knop, O. Z. Anorg. Allg.
Chem. 1997, 623, 104. (e) Chen, X.; Rickard, M. A.; Hull, J.
W. Jr.; Zheng, C.; Leugers, A.; Simoncic, P. Inorg. Chem.
2010, 49, 8684. (f) Wolff, M.; Meyer, J.; Feldmann, C.
Angew. Chem. Int. Ed. 2011, 50, 4970. (g) Wolff, M.; Okrut,
A.; Feldmann, C. Inorg. Chem. 2011, 50, 11683. (h) Vitske,
V.; Herrmann, H.; Enders, M.; Kaifer, E.; Himmel, H.-J.
Chem. Eur. J. 2012, 18, 14108. (i) Haller, H.; Schröder, J.;
Riedel, S. Angew. Chem. Int. Ed. 2013, 52, 4937. (j) Haller,
H.; Hog, M.; Scholz, F.; Scherer, H.; Krossing, I.; Riedel, S.
© Georg Thieme Verlag Stuttgart · New York
Synthesis 2014, 46, 740–747