J. Zhang et al. / Tetrahedron 67 (2011) 8800e8807
8807
4.2.20. 1-Phenyl-2-[2,4,6-tris(1-methylethyl)phenyl] ethanone (Table
3, entry 3). Light yellow solid; mp: 113e115 ꢀC, lit.:29 mp
113.5e114.5 ꢀC; 1H NMR (400 MHz, CDCl3)
7.60e7.58 (m, 1H), 7.52e7.48 (m, 2H), 7.03 (s, 1H), 4.44 (s, 2H,
CH2(CO)), 2.93e2.83 (m, 3H, CH(CH3)2), 1.27e1.17 (m, 18H, CH3); 13C
NMR (100 MHz, CDCl3) 197.7, 147.4, 147.1, 137.2, 133.1, 128.7, 128.1,
126.5, 121.0, 37.7, 34.2, 30.3, 24.1, 24.0.
References and notes
1. (a) Shen, T. Y. Angew. Chem., Int. Ed. Engl. 1972, 6, 460; (b) Lednicer, D.; Metscher,
L. A. The Organic Chemistry of Drug Synthesis; Wiley: New York, NY,1977; Vol.1, pp
85e99; Lednicer, D.; Metscher, L. A. The Organic Chemistry of Drug Synthesis;
Wiley: New York, 1977; Vol. 1; 267e280; Lednicer, D.; Metscher, L. A. The Organic
Chemistry of Drug Synthesis; Wiley: New York, NY, 1980; Vol. 2; p 63e84; (c) The
Merck Index, 11th ed.; Merck: Rahway, NJ, 1989; (d) Fuji, K. Chem. Rev. 1993, 93,
2037; (e) Bolm, C.; Hildebrand, J. P.; Muniz, K.; Hermanns, N. Angew. Chem., Int.
Ed. 2001, 40, 3284; (f) Nicole, D.; Jacques, P. R.; Kai, T. Eur. J. Org. Chem. 2005,1731;
(g) Shao, Z. H.; Zhang, H. B. Chin. J. Org. Chem. 2005, 25, 282.
d
8.08 (d, J¼7.6 Hz, 2H),
2. (a) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull. Chem. Soc. Jpn. 1984, 57,
242; (b) March, J. Aromatic nucleophilic substitution In Advanced Organic
Chemistry: Reactions, Mechanisms, and Structure; John: New York, NY, 1992;
Chapter 13, pp 641e676.
O
3. (a) Carfagna, C.; Musco, A.; Sallese, G.; Santi, R.; Fiorani, T. J. Org. Chem. 1991, 56,
261; (b) Durandetti, M.; Nedelec, J.-Y.; Perichon, J. J. Org. Chem. 1996, 61, 1748;
(c) Kuwajima, I.; Urabe, H. J. Am. Chem. Soc. 1982, 104, 6831; (d) Kuwajima, I.;
Nakamura, E. Acc. Chem. Res. 1985, 18, 181; (e) Stewart, J. D.; Fields, S. C.;
Kochhar, K. S.; Pinnick, H. W. J. Org. Chem. 1987, 52, 2110; (f) Shibata, I.; Baba, A.
Org. Prep. Proced. Int. 1994, 26, 85; (g) Finet, J. P. Chem. Rev. 1989, 89, 1487; (h)
Liu, C.; He, W.; Chen, M.; Lei, A. Org. Lett. 2007, 9, 5601; (i) Pandey, G.; Krishna,
A.; Girija, K.; Karthlkeyan, M. Tetrahedron Lett. 1993, 34, 6631.
4. (a) Barton, D. H. R.; Finet, J. P.; Khamsi, J.; Pichon, C. Tetrahedron Lett. 1986, 27,
3619; (b) Barton, D. H. R.; Donnelly, D. M. X.; Finet, J.-P.; Guiry, P. J. J. Chem. Soc.,
Perkin Trans. 1 1992, 1365.
4.2.21. 1-(1-Naphthalenyl)-2-[2,4,6-tris(1-methylethyl)phenyl] etha-
none (Table 3, entry 10). Slight yellow oil; 1H NMR (400 MHz, CDCl3)
d
8.59 (d, J¼8.3 Hz, 1H, ArH), 8.06 (d, J¼7.1 Hz, 1H, ArH), 7.98 (d,
5. (a) Giovannini, R.; Knochel, P. J. Am. Chem. Soc.1998,120,11186; (b) Duncton, M. A.
Z. J.; Estiarte, M. A.; Tan, D.; Kaub, C.; O’Mahony, D. J. R.; Johnson, R. J.; Cox, M.;
Edwards, W. T.; Wan, M.; Kincaid, J.; Kelly, M. G. Org. Lett. 2008, 10, 3259;
(c) Takahashi, H.; Inagaki, S.; Nishihara, Y.; Shibata, T.; Takagi, K. Org. Lett. 2006, 8,
3037; (d) Chowdhury, R. R.; Crane, A.; Fowler, C.; Kwong, P.; Kozak, C. M. Chem.
Commun. 2008, 94; (e) Yasuda, S.; Yorimitsu, H.; Oshima, K. Bull. Chem. Soc. Jpn.
2008, 81, 287; (f) Ohmiya, H.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2006,128,
1886.
6. Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108.
7. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382.
8. Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed.1997, 36,1740.
9. (a) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234; (b) Bellina, F.; Rossi,
R. Chem. Rev. 2010, 110, 1082; (c) Johansson, C. C. C.; Colacot, T. J. Angew. Chem.,
Int. Ed. 2010, 49, 676.
J¼8.2 Hz, 1H, ArH), 7.85 (d, J¼7.9 Hz, 1H, ArH), 7.55e7.12 (m, 3H, ArH),
7.09(s, 2H, ArH), 4.56 (s, 2H, CH2(CO)), 3.04e2.90 (m, 3H, CH(CH3)2),
1.30e1.21 (m, 18H, CH3). 13C NMR (100 MHz, CDCl3),
d 201.8, 147.5,
147.2, 136.1, 134.0, 132.6, 130.2, 128.4, 128.0, 127.1, 126.6, 126.5, 125.7,
124.3, 121.0, 41.2, 34.2, 30.4, 24.1, 24.0. HRMS (positive ESI) calcd for
C27H32NaO (MNaþ): 395.2351; found: 395.2349.
O
10. (a) Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219, 211; (b) Miura, M.; Satoh, T.
PalladiuminOrganicSynthesis; Springer: Berlin/Heidelberg, 2005;Vol.14; (c)Terao,
Y.; Fukuoka, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 2002, 43, 101.
11. (a) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122,
1360; (b) Moradi, W. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7996; (c)
Martyn, R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 7236.
12. (a) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473; (b) Culkin, D.
A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 5816; (c) Hama, T.; Liu, X.; Culkin,
D.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 11176; (d) Liu, X.; Hartwig, J. F. J. Am.
Chem. Soc. 2004, 126, 5182; (e) Vo, G. D.; Hartwig, J. F. Angew. Chem., Int. Ed.
2008, 47, 2127.
4.2.22. 1-(2-Methylphenyl)-2-[2,4,6-tris(1-methylethyl)phenyl] etha-
none (Table 3, entry 13). Yellow oil; 1H NMR (400 MHz, CDCl3)
d 7.84
13. (a) N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH: New York,
NY, 2006; (b) Wurtz, S.; Glorius, F. Acc. Chem. Res. 2008, 41, 1523; (c) Lin, L.; Li,
Y.; Du, W.; Deng, W. P. Tetrahedron Lett. 2010, 51, 3571.
(d, J¼7.6 Hz, 1H, ArH), 7.43e7.29 (m, 3H, ArH), 7.04 (s, 2H, ArH), 4.38
(s, 2H, CH2(CO)), 2.94e2.87 (m, 3H, CH(CH3)2), 2.48 (s, 3H, CH3),
14. Singh, R.; Nolan, S. P. J. Organomet. Chem. 2005, 690, 5832.
1.28e1.20 (m, 18H, CH3). 13C NMR (100 MHz, CDCl3),
d 201.8, 147.4,
15. (a) Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053; (b) Viciu,
M. S.; Germaneau, R. F.; Navarro-Fernandez, O.; Stevens, E. D.; Nolan, S. P.
Organometallics 2002, 21, 5470; (c) Cao, C. S.; Wang, L. L.; Cai, Z. Y.; Zhang, L. Q.;
Guo, J.; Pang, G. S.; Shi, Y. H. Eur. J. Org. Chem. 2011, 1570.
16. Viciu, M. S.; Kelly, R. A., III; Stevens, E. D.; Naud, F.; Studer, M.; Nolan, S. P. Org.
Lett. 2003, 5, 1479.
147.1, 138.3, 138.2, 132.1, 131.3, 128.1, 126.6, 125.7, 121.0, 40.7, 34.2,
30.3, 24.0, 21.2; HRMS (positive ESI) calcd for C24H32NaO (MNaþ):
359.2351; found: 359.2355.
17. Lavallo, V.; Canac, Y.; Prasang, C.; Donnadieu, B.; Bertrand, G. Angew. Chem.
2005, 117, 5851; Angew. Chem., Int. Ed. 2005, 44, 5705.
Acknowledgements
18. Matsubara, K.; Okazaki, H.; Senju, M. J. Organomet. Chem. 2006, 691, 3693.
19. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
20. (a) Ren, G. R.; Cui, X. L.; Yang, E. B.; Yang, F.; Wu, Y. J. Tetrahedron 2010, 66, 4022;
(b) Ren, G. R.; Cui, X. L.; Wu, Y. J. Eur. J. Org. Chem. 2010, 12, 2372.
21. Li, J. Y.; Cui, M. J.; Yu, A. J.; Wu, Y. J. J. Organomet. Chem. 2007, 692, 3732.
22. Suh, Y. S.; Lee, J. S.; Kim, S. H.; Rieke, R. D. J. Orgnomet. Chem. 2003, 684, 20.
23. Curtin, D. Y.; Crew, M. C. J. Am. Chem. Soc. 1954, 76, 3719.
We are grateful to the National Science Foundation of China
(Project 20772114) and the Innovation Fund for Outstanding
Scholar of Henan Province (Project 0621001100) for the financial
support given to this research.
24. Battace, A.; Feuerstein, M.; Lemhadri, M.; Zair, T.; Doucet, H.; Santelli, M. Eur. J.
Org. Chem. 2007, 3122.
25. Grasa, G. A.; Colacot, T. J. Org. Lett. 2007, 9, 5489.
26. Anstead, G. M.; Katzendllenbogen, S. A. J. Med. Chem. 1988, 31, 1754.
27. Nilsson, P.; Larhed, M.; Hallberg, A. J. Am. Chem. Soc. 2001, 123, 8217.
28. Xie, J. H.; Liu, S.; Huo, X. H.; Duan, H. F.; Fan, B. M.; Wang, L. X.; Zhou, Q. L. J. Org.
Chem. 2005, 70, 2967.
29. Fuson, R. C.; Armstrong, L. J.; Chadwick, D. H.; Kneisley, J. W.; Rowland, S. P.;
Shenk, W. J., Jr.; Soper, Q. F. J. Am. Chem. Soc. 1945, 67, 386.
Supplementary data
Supplementary data associated with this article can be found, in