Organometallics
Article
Tetrahedron Lett. 2007, 48, 1213−1216. (n) Guo, Y.; Tao, G.-H.;
Blumenfeld, A.; Shreeve, J. M. Organometallics 2010, 29, 1818−1823.
(5) (a) Galarini, R.; Musco, A.; Pontellini, R.; Santi, R. J. Mol. Catal.
1992, 72, L11−L13. (b) Huang, Z.; Liu, Z.; Zhou, J. S. J. Am. Chem.
Soc. 2011, 133, 15882−15885.
(6) (a) Sato, T.; Inoh, J.-i.; Kawamura, Y.; Kawamura, Y.; Miura, M.;
Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 2239−2246. (b) Moradi,
W. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7996−8002.
(c) Lee, S.; Beare, N. A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123,
8410−8411. (d) Jørgensen, M.; Lee, S.; Liu, X.; Wolkowski, J. P.;
Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 12557−12565. (e) Hama,
T.; Hartwig, J. F. Org. Lett. 2008, 10, 1545−1548. (f) Hama, T.;
Hartwig, J. F. Org. Lett. 2008, 10, 1549−1552.
(7) (a) Harrington, P. J.; Lodewijk, E. Org. Process Res. Dev. 1997, 1,
72−76. (b) Landoni, M. F.; Soraci, A. Curr. Drug Metab. 2001, 2, 37−
51. (c) Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2002, 41, 953−956.
(8) (a) Goossen, L. J. Chem. Commun. 2001, 669−670. (b) Liu, C.;
He, C.; Shi, W.; Chen, M.; Lei, A. Org. Lett. 2007, 9, 5601−5604.
(c) Dai, X.; Strotman, N. A.; Fu, G. C. J. Am. Chem. Soc. 2008, 130,
3302−3303. (d) Lundin, P. M.; Esquivias, J.; Fu, G. C. Angew. Chem.,
Int. Ed. 2009, 48, 154−156. (e) Lou, S.; Fu, G. C. J. Am. Chem. Soc.
2010, 132, 1264−1266. (f) Lundin, P. M.; Fu, G. C. J. Am. Chem. Soc.
2010, 132, 11027−11029. (g) Owston, N. A.; Fu, G. C. J. Am. Chem.
Soc. 2010, 132, 11908−11909.
(9) (a) Yamamoto, Y.; Takada, S.; Miyaura, N. Chem. Lett. 2006, 35,
704−705. (b) Yamamoto, Y.; Takada, S.; Miyaura, N. Chem. Lett.
2006, 35, 1368−1369. (c) Yamamoto, Y.; Takada, S.; Miyaura, N.;
Iyama, T.; Tachikawa, H. Organometallics 2009, 28, 152−160.
(10) Shiina, I.; Nakata, K.; Ono, K.; Onda, Y.-S.; Itagaki, M. J. Am.
Chem. Soc. 2010, 132, 11629−11641.
smoothly with silyl ketene acetals. Extension to an advanced
version based on the nature of the catalytic cycle and
enantioselection is in progress in our laboratory.
ASSOCIATED CONTENT
■
S
* Supporting Information
Text, tables, and figures providing experimental details, spectral
and/or analytical data of the products, and X-ray data. This
material is available free of charge via the Internet at http://
AUTHOR INFORMATION
■
Corresponding Author
6560.
ACKNOWLEDGMENTS
■
This work was supported by the Global COE Program (Project
No. B01: Catalysis as the Basis for Innovation in Materials
Science) from the Ministry of Education, Culture, Sports,
Science and Technology, Japan. We thank S. Oka, A.
Tokumitsu, K. Owada, and A. Nagao of the Instrumental
Analysis Division, Equipment Management Center, Creative
Research Institution, Hokkaido University, for technical
assistance in MS analyses.
(11) (a) Nagib, D. A.; Scott, M. E.; MacMillan, D. C. J. Am. Chem.
Soc. 2009, 131, 10875−10877. (b) Allen, A. E.; MacMillan, D. C. J.
Am. Chem. Soc. 2010, 132, 4986−4987. (c) Harvey, J. S.; Simonovich,
S. P.; Jamison, C. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2011, 133,
13782−13785. (d) Bigot, A.; Williamson, A. E.; Gaunt, M. J. J. Am.
Chem. Soc. 2011, 133, 13778−13781.
REFERENCES
■
(1) For recent reviews: (a) Culkin, D. A.; Hartwig, J. F. Acc. Chem.
Res. 2003, 36, 234−245. (b) Bellina, F.; Rossi, R. Chem. Rev. 2010,
110, 1082−1146. (c) Burtoloso, A. C. Synlett 2009, 320−327.
(d) Johansson, C. C. C.; Colacot, T. J. Angew. Chem., Int. Ed. 2010,
49, 676−707.
(2) (a) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew.
Chem., Int. Ed. 1997, 36, 1740−1742. (b) Palucki, M.; Buchwald, S. L.
J. Am. Chem. Soc. 1997, 119, 11108−11109. (c) Hamann, B. C.;
Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382−12383.
(12) Although we have no clear reason for this result, effects of
halides are reviewed. Lautens, M.; Fagnou, K. Angew. Chem., Int. Ed.
2002, 41, 26−47.
(13) Hutt, A. J.; Caldweell, J. J. Pharm. Pharmacol. 1983, 35, 693−
704.
(3) (a) Åhman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.;
Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918−1919. (b) Hamada,
T.; Chieffi, A.; Åhman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124,
1261−1268. (c) Spielvogel, D. J.; Buchwald, S. L. J. Am. Chem. Soc.
2002, 124, 3500−3501. (d) Spielvogel, D. J.; Davis, W. M.; Buchwald,
S. L. Organometallics 2002, 21, 3833−3836. (e) Chen, G.; Kwong, F.
Y.; Chan, H. O.; Yu, W.-Y.; Chan, A. S. C. Chem. Commun. 2006,
1413−1415. (f) Liao, X.; Weng, Z.; Hartwig, J. F. J. Am. Chem. Soc.
2008, 130, 195−200. (g) Taylor, A. M.; Altman, R. A.; Buchwald, S. L.
J. Am. Chem. Soc. 2009, 131, 9900−9901.
(4) (a) Kuwajima, I.; Urabe, H. J. Am. Chem. Soc. 1982, 104, 6831−
6833. (b) Carfagna, C.; Musco, A.; Sallese, G.; Santi, R.; Fiorani, T. J.
Org. Chem. 1991, 56, 261−263. (c) Sakamoto, T.; Kondo, Y.;
Masumoto, K.; Yamanaka, H. Heterocycles 1993, 36, 2509−2512.
(d) Sakamoto, T.; Kondo, Y.; Masumoto, K.; Yamanaka, H. J. Chem.
Soc., Perkin Trans. 1 1994, 235−236. (e) Koch, K.; Melvin, L. S. Jr.;
Reiter, L. A.; Biggers, M. S.; Showell, H. J.; Griffiths, R. J.; Pettipher,
E. R.; Cheng, J. B.; Milici, A. J.; Breslow, R.; Conklyn, M. J.; Smith,
M. A.; Hacjman, B. C.; Doherty, N. S.; Salter, E.; Farrell, C. A.;
Schultz, G. J. Med. Chem. 1994, 37, 3197−3199. (f) Agnelli, F.;
Sulikowski, G. A. Tetrahedron Lett. 1998, 39, 8807−8810. (g) Hama,
T.; Liu, X.; Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125,
11176−11177. (h) Liu, X.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126,
5182−5191. (i) Chae, J.; Yun, J.; Buchwald, S. L. Org. Lett. 2004, 6,
4809−4812. (j) Iwama, T.; Rawal, V. H. Org. Lett. 2006, 8, 5725−
5728. (k) Su, W.; Raders, S.; Verkade, J. G.; Liao, X.; Hartwig, J. F.
Angew. Chem., Int. Ed. 2006, 45, 5852−5855. (l) Johnson, P. D.; Sohn,
J.-H.; Rawal, V. H. J. Org. Chem. 2006, 71, 7899−7902.
(m) Chobanian, H. R.; Liu, P.; Chioda, M. D.; Guo, Y.; Lin, L. S.
(14) The Tl+ cation has a high stability constant for halide ions.
Miyaura, N. Bull. Chem. Soc. Jpn. 2008, 81, 1535−1553.
(15) Transmetalation may proceed via a six-membered metathesis.
Wang, B.; Sun, H.-X.; Sun, Z.-H. J. Org. Chem. 2009, 74, 1781−1784.
(16) (a) Gambs, C.; Consiglio, G.; Togni, A. Helv. Chem. Acta 2001,
84, 3105−3126. (b) Roy, A. H.; Hartwig, J. F. Organometallics 2004,
23, 194−202.
(17) (a) Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999,
121, 5450−5458. (b) Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc.
2001, 123, 5816−5817. (c) Culkin, D. A.; Hartwig, J. F. Organo-
metallics 2004, 23, 3398−3416.
6327
dx.doi.org/10.1021/om200945q|Organometallics 2011, 30, 6323−6327