Bing Wang et al.
FULL PAPERS
thesis, 1st edn., (Ed.: E. Negishi), John Wiley & Sons
Inc., New York, 2002; d) P. Espinet, A. M. Echavarren,
Angew. Chem. 2004, 116, 4808; Angew. Chem. Int. Ed.
2004, 43, 4704.
[17] N. Morohashi, T. Kitahara, T. Arima, S. Tanaka, Y.
Ohba, T. Hattori, Org. Lett. 2008, 10, 2845.
[18] L. Zhu, S. H. Shabbir, M. Gray, V. M. Lynch, S. Sorey,
E. V. Anslyn, J. Am. Chem. Soc. 2006, 128, 1222.
[19] J. M. Herbert, Tetrahedron Lett. 2004, 45, 817.
[20] M. Prieto, E. Zurita, E. Rosa, L. Munoz, P. Lloyd-Wil-
liams, E. Giralt, J. Org. Chem. 2004, 69, 6812.
[21] a) N. Jaber, D. Gelman, H. Schumann, S. Dechert, J.
Blum, Eur. J. Org. Chem. 2002, 1628. Triethylaluminum
was also shown to couple with aryl bromides under the
assistance of a stoichiometric amount of lanthanide,
however, whether this system tolerated acidic functions
was not revealed: b) M. Shenglof, D. Gelman, G. A.
Molander, J. Blum, Tetrahedron Lett. 2003, 44, 8593.
[22] N. A. Bumagin, E. V. Luzikova, J. Organomet. Chem.
1997, 532, 271.
[8] a) D. S. Matteson, Tetrahedron 1989, 45, 1859; b) J. A.
Marshall, B. A. Johns, J. Org. Chem. 1998, 63, 7885;
c) J. A. Soderquist, J. C. Justo de Pomar, Tetrahedron
Lett. 2000, 41, 3537.
[9] For leading references, see: a) G. A. Molander, T. Ito,
Org. Lett. 2001, 3, 393; b) G. A. Molander, C.-S. Yun,
M. Ribagorda, B. Biolatto, J. Org. Chem. 2003, 68,
5534. For excellent reviews of potassium organotrifluoro-
ACHTUNGTRENNUNGborates, see: c) G. A. Molander, N. Ellis, Acc. Chem.
Res. 2007, 40, 275; d) S. Darses, J.-P. Genet, Chem. Rev.
2008, 108, 288.
[10] a) G. Zou, Y. K. Reddy, J. R. Falck, Tetrahedron Lett.
2001, 42, 7213; b) G. A. Molander, C.-S. Yun, Tetrahe-
dron 2002, 58, 1465; c) N. Kataoka, Q. Shelby, J. P.
Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553.
For the first example of Suzuki coupling using alkylbor-
onic acid, see: d) Y. Q. Mu, R. A. Gibbs, Tetrahedron
Lett. 1995, 36, 5669. Suzuki coupling using alkylboro-
nates: e) M. Sato, N. Miyaura, A. Suzuki, Chem. Lett.
1989, 1405; f) M. B. Andrus, C. Song, Org. Lett. 2001, 3,
3761. Ate-complex of boronate: g) G. Zou, J. R. Falck,
Tetrahedron Lett. 2001, 42, 5817.
[11] Trialkylboranes were conveniently prepared from the
corresponding Grignard reagents with boron trifluoride
etherate: a) H. C. Brown, U. S. Racherla, J. Org. Chem.
1986, 51, 427. Selected applications of trialkylboranes:
b) D. A. Evans, J. V. Nelson, E. Vogel, T. R. Taber, J.
Am. Chem. Soc. 1981, 103, 3099; c) W. Oppolzer, I. Ro-
driguez, C. Starkemann, E. Walther, Tetrahedron Lett.
1990, 31, 5019; d) T. Ukon, T. Harada, Eur. J. Org.
Chem. 2008, 4405.
[12] a) T. Harada, T. Yoshida, A. Inoue, M. Takeuchi, A.
Oku, Synlett 1995, 283; b) S. J. OꢀConnor, K. J. Barr, L.
Wang, B. K. Sorensen, A. S. Tasker, H. Sham, S.-C. Ng,
J. Cohen, E. Devine, S. Cherian, B. Saeed, H. Zhang,
J. Y. Lee, R. Warner, S. Tahir, P. Kovar, P. Ewing, J.
Alder, M. Mitten, J. Leal, K. Marsh, J. Bauch, D. J.
Hoffman, S. M. Sebti, S. H. Rosenberg, J. Med. Chem.
1999, 42, 3701; c) T. Gꢃngçr, Y. Chen, R. Golla, Z. Ma,
J. R. Corte, J. P. Northrop, B. Bin, J. K. Dickson, T.
Stouch, R. Zhou, S. E. Johnson, R. Seethala, J. H. M.
Feyen, J. Med. Chem. 2006, 49, 2440; d) L. R. Marrison,
J. M. Dickinson, I. J. S. Fairlamb, Bioorg. Med. Chem.
Lett. 2002, 12, 3509; e) I. J. S. Fairlamb, L. R. Marrison,
J. M. Dickinson, F.-J. Lu, J.-P. Schmidt, Bioorg. Med.
Chem. 2004, 12, 4285.
[23] See, for example: M. R. Netherton, C. Dai, K. Neu-
schꢃtz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099.
[24] G. A. Molander, B. W. Katona, F. Machrouhi, J. Org.
Chem. 2002, 67, 8416.
[25] L. H. Toporcer, R. E. Dessy, S. I. E. Green, Inorg.
Chem. 1965, 4, 1649.
[26] a) T. Flessner, S. Doye, J. Prakt. Chem. 1999, 341, 186;
b) F. Lehmann, Synlett 2004, 2447.
[27] K. Matos, J. A. Soderquist, J. Org. Chem. 1998, 63, 461.
[28] Similarly, cesium alkyl carbonates underwent smooth
alkylation in the synthesis of mixed dialkyl carbonates
using Cs2CO3 as the base, see: F. Chu, E. E. Dueno,
K. W. Jung, Tetrahedron Lett. 1999, 40, 1847.
[29] R. Ferracciolo, D. Carenzi, E. Motti, M. Catellani, J.
Am. Chem. Soc. 2006, 128, 722. In our case although
we were not able to separate cross-coupling product
from a side product, Ar-ethyl signals were observed in
1
the H NMR of the partially purified mixture, while the
other component has only aromatic protons. The latter
was assigned as dimerization side product as it showed
strong fluorescence and it was not reductive de-halo-
genation side product by comparison with an authentic
sample.
[30] a) B. J. Backes, J. A. Ellman, J. Am. Chem. Soc. 1994,
116, 11171; b) J. A. Soderquist, I. Kock, M. E. Estrella,
Org. Process Res. Dev. 2006, 10, 1076.
[31] T. Oh-e, N. Miyaura, A. Suzuki, J. Org. Chem. 1993, 58,
2201.
[32] W.-C. Shieh, J. A. Carlson, J. Org. Chem. 1992, 57, 379.
[33] a) P. G. M. Wuts, T. W. Greene, Greeneꢀs Protective
Groups in Organic Synthesis, 4th edn., John Wiley &
Sons, Hoboken, NJ, 2007; b) P. J. Kocienski, Protecting
Groups, 3rd edn., Thieme, New York, 2005.
[34] a) D. Brꢃckner, F.-T. Hafner, V. Li, C. Schmeck, J.
Telser, A. Vakalopoulos, G. Wirtz, Bioorg. Med. Chem.
Lett. 2005, 15, 3611; b) H. Bischoff, F.-T. Hafner, C.
Schmeck, J. Telser, A. Vakalopoulos, G. Wirtz, M.
Bauser, D. Brꢃckner, M. Wuttke, WO Patent, 2004/
039453 A2.
[13] a) P. S. Baran, T. J. Maimone, J. M. Richter, Nature
2007, 446, 404; b) R. W. Hoffmann, Synthesis 2006,
3531.
[14] Suzuki coupling of boronic acids in the presence of
acidic functions has been reported: a) Y. Gong, W. He,
Org. Lett. 2002, 4, 3803; b) K. W. Anderson, S. L. Buch-
wald, Angew. Chem. 2005, 117, 6329; Angew. Chem.
Int. Ed. 2005, 44, 6173.
[35] T. Sassa, G. Niwa, H. Unno, M. Ikeda, Y. Miura, Tetra-
hedron Lett. 1974, 3941.
[36] CCDC 704508 contains the supplementary crystallo-
graphic data for this paper. These data can be obtained
free of charge from The Cambridge Crystallographic
[15] G. Manolikakes, M. A. Schade, C. M. Hernandez, H.
Mayr, P. Knochel, Org. Lett. 2008, 10, 2765.
[16] L. H. Toporcer, R. E. Dessy, S. I. E. Green, J. Am.
Chem. Soc. 1965, 87, 1236.
422
ꢁ 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2009, 351, 415 – 422