The Journal of Organic Chemistry
Article
(9) Shen, Z.-L.; Jiang, X.-Z. J. Mol. Catal. A: Chem. 2004, 213, 193−
Foundation of Zhejiang Provincial Top Key Discipline (No.
1000612001) is greatly appreciated.
198.
(10) da Silva, R. A.; Estevam, I. H. S.; Bieber, L. W. Tetrahedron Lett.
2007, 48, 7680−7682.
REFERENCES
(11) Hanada, S.; Motoyama, Y.; Nagashima, H. Eur. J. Org. Chem.
2008, 4097−4100.
■
(1) For reviews on the NHC−Pd complex-catalyzed coupling
reactions, see: (a) Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H.
M.; Yang, C.-L.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69−82.
(b) Kantchev, E. A. B.; O’Brien, C. J.; Organ, M. G. Angew. Chem., Int.
Ed. 2007, 46, 2768−2813. (c) Marion, N.; Nolan, S. P. Acc. Chem. Res.
(12) Lee, B. K.; Biscoe, M. R.; Buchwald, S. L. Tetrahedron Lett.
2009, 50, 3672−3674.
(13) Tu, T.; Fang, W.-W.; Jiang, J. Chem. Commun. 2011, 47, 12358−
12360.
(14) Beller, M.; Breindl, C.; Riermeier, T. H.; Tillack, A. J. Org. Chem.
2001, 66, 1403−1412.
2008, 41, 1440−1449. (d) Wurtz, S.; Glorius, F. Acc. Chem. Res. 2008,
̈
41, 1523−1533. (e) Fortman, G. C.; Nolan, S. P. Chem. Soc. Rev. 2011,
40, 5151−5169. (f) Valente, C.; Çalimsiz, S.; Hoi, K. H.; Mallik, D.;
Sayah, M.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 3314−3332.
(2) For NHC−metal complexes derived from proline and their
applications, see: (a) Tang, Y.-Q.; Lu, J.-M.; Wang, X.-R.; Shao, L.-X.
Tetrahedron 2010, 66, 7970−7974. (b) Ma, M.-T.; Lu, J.-M. Appl.
Organometal. Chem. 2012, 26, 175−179 and references cited therein.
(3) For a well-defined NHC−Pd(II)−Im complex and its
applications, see: (a) Zhu, L.; Gao, T.-T.; Shao, L.-X. Tetrahedron
2011, 67, 5150−5155. (b) Zhu, L.; Ye, Y.-M.; Shao, L.-X. Tetrahedron
2012, 68, 2414−2420. (c) Xiao, Z.-K.; Shao, L.-X. Synthesis 2012, 44,
711−716. (d) Wang, Z.-Y.; Chen, G.-Q.; Shao, L.-X. J. Org. Chem.
2012, 77, 6608−6614 and references cited therein.
(4) (a) Muzart, J. Tetrahedron 2009, 65, 8313−8323 and references
therein. (b) Romero, M.; Harrak, Y.; Basset, J.; Orue, J. A.; Pujol, M.
́
D. Tetrahedron 2009, 65, 1951−1956. (c) Li, Y.-M.; Xie, Y.-S.; Zhang,
R.; Jin, K.; Wang, X.-N.; Duan, C.-Y. J. Org. Chem. 2011, 76, 5444−
5449.
(5) For some recent selected examples on the NHC−Pd complex-
catalyzed C−N bond formation reactions, see: (a) Winkelmann, O.
H.; Riekstins, A.; Nolan, S. P.; Navarro, O. Organometallics 2009, 28,
5809−5813. (b) Jin, Z.; Guo, S.-X.; Gu, X.-P.; Qiu, L.-L.; Song, H.-B.;
Fang, J.-X. Adv. Synth. Catal. 2009, 351, 1575−1585. (c) Hoi, K. H.;
Calimsiz, S.; Froese, R. D. J.; Hopkinson, A. C.; Organ, M. G. Chem.
Eur. J. 2011, 17, 3086−3090. (d) Marion, N.; Navarro, O.; Ecarnot, E.
C.; Bell, A.; Amoroso, D.; Nolan, S. P. Chem. Asian J. 2010, 841−846.
(e) Meiries, S.; Chartoire, A.; Slawin, A. M. Z.; Nolan, S. P.
Organometallics 2012, 31, 3402−3409. (f) Chartoire, A.; Frogneux, X.;
Boreux, A.; Slawin, A. M. Z.; Nolan, S. P. Organometallics 2012, 31,
6947−6951 and references cited therein.
(6) For some more recent selected papers on C−N coupling, see:
(a) Ali, A.; Saha, P.; Punniyamurthy, T. Synthesis 2010, 908−910.
(b) Tao, C.-Z.; Liu, W.-W.; Sun, J.-Y.; Cao, Z.-L.; Li, H.; Zhang, Y.-F.
Synthesis 2010, 1280−1284. (c) Wang, Y.-F.; Zeng, J.-H.; Cui, X.-R.
Chin. J. Org. Chem. 2010, 30, 181−199. (d) Lundgren, R. J.; Peters, B.
D.; Alsabeh, P. G.; Stradiotto, M. Angew. Chem., Int. Ed. 2010, 49,
4071−4074. (e) Lundgren, R. J.; Sappong-Kumankumah, A.;
Stradiotto, M. Chem.Eur. J. 2010, 16, 1983−1991. (f) Hu, Y.-L.;
Wang, P.-C.; Chen, T.; Lu, M. J. Chin. Chem. Soc. 2010, 57, 604−611.
(g) Huang, M.-N.; Lin, X.-Q.; Zhu, X.-H.; Peng, W.-L.; Xie, J.-W.;
Wan, Y.-Q. Eur. J. Org. Chem. 2011, 4523−4527. (h) Yang, K.; Qiu, Y.-
T.; Li, Z.; Wang, Z.-Y.; Jiang, S. J. Org. Chem. 2011, 76, 3151−3159.
(i) Reddy, V. P.; Vijay Kumar, A.; Rama Rao, K. Tetrahedron Lett.
2011, 52, 777−780. (j) Maejima, T.; Shimoda, Y.; Nozaki, K.; Mori, S.;
Sawama, Y.; Monguchi, Y.; Sajiki, H. Tetrahedron 2012, 68, 1712−
1722. (k) Maligres, P. E.; Krska, S. W.; Dormer, P. G. J. Org. Chem.
2012, 77, 7646−7651. (l) Harsha Vardhan Reddy, K.; Satish, G.;
Ramesh, K.; Karnakar, K.; Nageswar, Y. V. D. Tetrahedron Lett. 2012,
53, 3061−3065.
(7) (a) Nasipuri, D.; Bhattacharyya, A.; Hazra, B. G. Chem. Commun.
1971, 660−661. (b) Perrin, D. D.; Armarego, W. L. F. Purification of
Laboratory Chemicals, 3rd ed.; Pergamon: Oxford, 1988. (c) Toffano,
M.; Legros, J.-Y.; Fiaud, J.-C. Tetrahedron Lett. 1997, 38, 77−80.
(d) Cho, Y. H.; Park, J. C. Tetrahedron Lett. 1997, 38, 8331−8334.
(e) Sharma, A.; Mehta, V. P.; Van der Eycken, E. Tetrahedron 2008,
64, 2605−2610.
(8) Filali, E.; Lloyd-Jones, G. C.; Sale, D. A. Synlett 2009, 205−208
and references cited therein.
D
dx.doi.org/10.1021/jo301811n | J. Org. Chem. XXXX, XXX, XXX−XXX