3502
L. Ackermann et al.
SPECIAL TOPIC
(147 mg, 1.00 mmol) to give 3v as an off-white solid; yield: 152 mg
(72%); mp 52.3–53.1 °C. The spectral data were in accordance with
those reported in the literature.42
Miura, M. Chem. Eur. J. 2009, 15, 3674. (s) Campeau,
L.-C.; Stuart, D. R.; Leclerc, J.-P.; Bertrand-Laperle, M.;
Villemure, E.; Sun, H.-Y.; Lasserre, S.; Guimond, N.;
Lecavallier, M.; Fagnou, K. J. Am. Chem. Soc. 2009, 131,
3291. (t) Roger, J.; Požgan, F.; Doucet, H. J. Org. Chem.
2009, 74, 1179; and references cited therein.
IR (ATR): 3414, 3054, 2917, 1587, 1503, 1449, 1303, 1228, 1104,
825 cm–1.
1H NMR (300 MHz, CDCl3): d = 8.20 (br, s, 1 H), 8.08 (d,
J = 7.7 Hz, 1 H), 7.54 (s, 1 H), 7.48–7.23 (m, 3 H), 6.79 (s, 1 H),
4.04 (s, 3 H), 2.60 (s, 3 H).
13C NMR (75 MHz, CDCl3): d = 145.3, 139.4, 129.4, 127.9, 125.4,
124.3, 123.5, 120.4, 119.1, 112.5, 110.9, 107.6, 55.4, 21.9.
(5) For examples of rhodium-catalyzed direct arylations, see:
(a) Oi, S.; Fukita, S.; Inoue, Y. Chem. Commun. 1998, 2439.
(b) Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Limmert,
M. E. Angew. Chem. Int. Ed. 2003, 42, 112. (c) Oi, S.;
Watanabe, S.; Fukita, S.; Inoue, Y. Tetrahedron Lett. 2003,
44, 8665. (d) Lewis, J. C.; Wiedemann, S. H.; Bergman,
R. G.; Ellman, J. A. Org. Lett. 2004, 6, 35. (e) Wang, X.;
Lane, B. S.; Sames, D. J. Am. Chem. Soc. 2005, 127, 4996.
(f) Wiedemann, S. H.; Lewis, J. C.; Ellman, J. A.; Bergman,
R. G. J. Am. Chem. Soc. 2006, 128, 2452. (g) Lewis, J. C.;
Wu, J. Y.; Bergman, R. G.; Ellman, J. A. Angew. Chem. Int.
Ed. 2006, 45, 1589. (h) Yanagisawa, S.; Sudo, T.; Noyori,
R.; Itami, K. J. Am. Chem. Soc. 2006, 128, 11748.
MS (EI, 70 eV): m/z (%) = 211 (100) [M]+, 196 (77), 168 (42), 166
(29), 139 (5), 105 (7).
HRMS (EI): m/z calcd for C14H13NO: 211.0997; found: 211.0975.
Acknowledgment
Support by the DFG is gratefully acknowledged.
(i) Proch, S.; Kempe, R. Angew. Chem. Int. Ed. 2007, 46,
3135. (j) Vogler, T.; Studer, A. Org. Lett. 2008, 10, 129.
(k) Yanagisawa, S.; Sudo, T.; Noyori, R.; Itami, K.
Tetrahedron 2008, 64, 6073. (l) Zhao, X.; Yu, Z. J. Am.
Chem. Soc. 2008, 130, 8136. (m) Berman, A. M.; Lewis,
J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008,
130, 14926.
References
(1) Modern Arylation Methods; Ackermann, L., Ed.; Wiley-
VCH: Weinheim, 2009.
(2) For recent reviews, see : (a) Kakiuchi, F.; Kochi, T.
Synthesis 2008, 3013. (b) Li, B.-J.; Yang, S.-D.; Shi, Z.-J.
Synlett 2008, 949. (c) Lewis, J. C.; Bergman, R. G.; Ellman,
J. A. Acc. Chem. Res. 2008, 41, 1013. (d) Satoh, T.; Miura,
M. Top. Organomet. Chem. 2007, 24, 61. (e) Ackermann,
L. Top. Organomet. Chem. 2007, 24, 35. (f) Alberico, D.;
Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
(g) Pascual, S.; de Mendoza, P.; Echavarren, A. M. Org.
Biomol. Chem. 2007, 5, 2727. (h) Campeau, L.-C.; Stuart,
D. R.; Fagnou, K. Aldrichimica Acta 2007, 40, 35.
(i) Ackermann, L. Synlett 2007, 507. (j) Daugulis, O.;
Zaitsev, V. G.; Shabashov, D.; Pham, Q. N.; Lazareva, A.
Synlett 2006, 3382. (k) Yu, J.-Q.; Giri, R.; Chen, X. Org.
Biomol. Chem. 2006, 4041.
(6) Ackermann, L.; Vicente, R. In Modern Arylation Methods;
Ackermann, L., Ed.; Wiley-VCH: Weinheim, 2009, 311.
(7) For ruthenium-catalyzed direct arylations, see: (a) Oi, S.;
Fukita, S.; Hirata, N.; Watanuki, N.; Miyano, S.; Inoue, Y.
Org. Lett. 2001, 3, 2579. (b)Ackermann, L. Org. Lett. 2005,
7, 3123. (c) Kakiuchi, F.; Matsuura, Y.; Kan, S.; Chatani, N.
J. Am. Chem. Soc. 2005, 127, 5936. (d) Oi, S.; Aizawa, E.;
Ogino, Y.; Inoue, Y. J. Org. Chem. 2005, 70, 3113.
(e) Ackermann, L.; Althammer, A.; Born, R. Angew. Chem.
Int. Ed. 2006, 45, 2619. (f) Ackermann, L.; Althammer, A.;
Born, R. Synlett 2007, 2833. (g) Oi, S.; Funayama, R.;
Hattori, T.; Inoue, Y. Tetrahedron 2008, 64, 6051.
(h) Ackermann, L.; Althammer, A.; Born, R. Tetrahedron
2008, 64, 6115. (i) Ackermann, L.; Vicente, R.; Althammer,
A. Org. Lett. 2008, 10, 2299. (j) Deng, G.; Zhao, L.; Li,
C.-J. Angew. Chem. Int. Ed. 2008, 47, 6278. (k) Özdemir,
I.; Demir, S.; Cetinkaya, B.; Gourlaouen, C.; Maseras, F.;
Bruneau, C.; Dixneuf, P. H. J. Am. Chem. Soc. 2008, 130,
1156. (l) Oi, S.; Sasamoto, H.; Funayama, R.; Inoue, Y.
Chem. Lett. 2008, 37, 994. (m) Ackermann, L.; Mulzer, M.
Org. Lett. 2008, 10, 5043; and references cited therein.
(8) For further examples of direct arylations catalyzed by other
metals, see: (a) Fujita, K.; Nonogawa, M.; Yamaguchi, R.
Chem. Commun. 2004, 1926. (b) Join, B.; Yamamoto, T.;
Itami, K. Angew. Chem. Int. Ed. 2009, 48, 3644. (c) Do,
H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.
(d) Ackermann, L.; Potukuchi, H. K.; Landsberg, D.;
Vicente, R. Org. Lett. 2008, 10, 3081. (e) Yoshizumi, T.;
Tsurugi, H.; Satoh, T.; Miura, M. Tetrahedron Lett. 2008,
49, 1598. (f) Do, H.-Q.; Kashif Khan, R. M.; Daugulis, O.
J. Am. Chem. Soc. 2008, 130, 15185. (g) Phipps, R. J.;
Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130,
8172. (h) Norinder, J.; Matsumoto, A.; Yoshikai, N.;
Nakamura, E. J. Am. Chem. Soc. 2008, 130, 5858.
(3) Miura, M.; Satoh, T. In Modern Arylation Methods;
Ackermann, L., Ed.; Wiley-VCH: Weinheim, 2009, 335.
(4) For selected recent examples of palladium-catalyzed direct
arylations, see: (a) Okazawa, T.; Satoh, T.; Miura, M.;
Nomura, M. J. Am. Chem. Soc. 2002, 124, 5286. (b) Park,
C.-H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.;
Gevorgyan, V. Org. Lett. 2004, 6, 1159. (c) Kalyani, D.;
Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem.
Soc. 2005, 127, 7330. (d) Campeau, L.-C.; Rousseaux, S.;
Fagnou, K. J. Am. Chem. Soc. 2005, 127, 18020.
(e) Daugulis, O.; Zaitsev, V. G. Angew. Chem. Int. Ed. 2005,
44, 4046. (f) Deprez, N. R.; Kalyani, D.; Krause, A.;
Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 4972.
(g) Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128,
16496. (h) Turner, G. L.; Morris, J. A.; Greaney, M. F.
Angew. Chem. Int. Ed. 2007, 46, 7996. (i) Iwasaki, M.;
Yorimitsu, H.; Oshima, K. Chem. Asian J. 2007, 2, 1430.
(j) Ackermann, L.; Vicente, R.; Born, R. Adv. Synth. Catal.
2008, 350, 741. (k) Lebrasseur, N.; Larrosa, I. J. Am. Chem.
Soc. 2008, 130, 2926. (l) Campeau, L.-C.; Bertrand-
Laperle, M.; Leclerc, J.-P.; Villemure, E.; Gorelsky, S.;
Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3276.
(m) Požgan, F.; Roger, J.; Doucet, H. ChemSusChem 2008,
1, 404. (n) Cusati, G.; Djakovitch, L. Tetrahedron Lett.
2008, 49, 2499. (o) Bellina, F.; Benelli, F.; Rossi, R. J. Org.
Chem. 2008, 73, 5529. (p) Ackermann, L.; Althammer, A.;
Fenner, S. Angew. Chem. Int. Ed. 2009, 48, 201.
(i) Yoshikai, N.; Matsumoto, A.; Norinder, J.; Nakamura, E.
Angew. Chem. Int. Ed. 2009, 48, 2925. (j) Canivet, J.;
Yamaguchi, J.; Ban, I.; Itami, K. Org. Lett. 2009, 11, 1733.
(k) Hachiya, H.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett.
2009, 11, 1737.
(9) Ames, D. E.; Bull, D. Tetrahedron 1982, 38, 383.
(10) Ames, D. E.; Opalko, A. Synthesis 1983, 234.
(q) Ackermann, L.; Barfüßer, S. Synlett 2009, 808.
(r) Miyasaka, M.; Fukushima, A.; Satoh, T.; Hirano, K.;
Synthesis 2009, No. 20, 3493–3503 © Thieme Stuttgart · New York