Paper
RSC Advances
was washed with ethyl acetate (20 mL). The ltrate was
neutralized by the addition of a saturated solution of NaHCO3
(10 mL) and ammonium chloride (20 mL) with constant stirring
and then extracted with ethyl acetate (3 ꢂ 20 mL). The organic
layer was concentrated under reduced pressure and the residue
was puried by ash column chromatography to afford the
desired product 4a.
M. K. Tse, S. Zhou, M.-M. Pohl, J. Radnik, S. Hubner,
K. Jahnisch, A. Bruckner and M. Beller, J. Am. Chem. Soc.,
2009, 131, 1775–1779; (c) F. Shi, M. K. Tse, X. Cui,
D. Gordes, D. Michalik, K. Thurow, Y. Deng and M. Beller,
Angew. Chem., Int. Ed., 2009, 48, 5912–5915; (d)
A. J. A. Watson, A. C. Maxwell and J. M. J. Williams, J. Org.
Chem., 2011, 76, 2328–2331; (e) X. C. Yu, C. Z. Liu, L. Jiang
and Q. Xu, Org. Lett., 2011, 13, 6184–6187; (f) P. Qu,
C. Sun, J. Ma and F. Li, Adv. Synth. Catal., 2014, 356, 447–459.
7 (a) J. D. Hicks, A. M. Hyde, A. M. Cuezva and S. L. Buchwald,
J. Am. Chem. Soc., 2009, 131, 16720–16734; (b) S. Shekhar,
T. B. Dunn, B. J. Kotecki, D. K. Montavon and S. C. Cullen,
J. Org. Chem., 2011, 76, 4552–4563.
8 (a) J. V. Ruppel, R. M. Kamble and X. P. Zhang, Org. Lett.,
2007, 9, 4889–4892; (b) B. Kalita, A. A. Lamar and
K. M. Nicholas, Chem. Commun., 2008, 44, 4291–4293; (c)
H. J. Lu, H. L. Jiang, Y. Hu, L. Wojtas and X. P. Zhang,
Chem. Sci., 2011, 2, 2361–2366; (d) B. Xiao, T. J. Gong,
J. Xu, Z. J. Liu and L. Liu, J. Am. Chem. Soc., 2011, 133,
1466–1474; (e) Q. Z. Zheng, Y. P. Liang, C. Qin and N. Jiao,
Chem. Commun., 2013, 49, 5654–5656; (f) H. Q. Zhao,
Y. P. Shang and W. P. Su, Org. Lett., 2013, 15, 5106–5109;
(g) C. Pan, A. Abdukader, J. Han, Y. Cheng and C. Zhu,
Chem.–Eur. J., 2014, 20, 3606–3609; (h) Y. K. Kumar,
G. R. Kumar and M. S. Reddy, J. Org. Chem., 2014, 79, 823–
828.
Acknowledgements
Financial supports from the National Natural Science Founda-
tion of China (No. 21462021) and Scientic Research Fund of
Education Department of Jiangxi Province (KJLD13022) and Key
Laboratory of Functional Small Organic Molecule, Ministry of
Education (No. KLFS-KF-201213) are gratefully acknowledged.
References
1 (a) A. Scozzafava, T. Owa, A. Mastrolorenzo and
C. T. Supuran, Curr. Med. Chem., 2003, 10, 925–953; (b)
D. A. Smith and R. M. Jones, Curr. Opin. Drug Discovery
Dev., 2008, 11, 72–79.
2 (a) C. T. Supuran, A. Casini and A. Scozzafava, Med. Res. Rev.,
2003, 5, 535–558; (b) N. S. M. Reddy, R. Mallireddigari,
K. G. Cosenza, S. C. Bell, E. P. Reddy and M. V. R. Reddy,
Bioorg. Med. Chem. Lett., 2004, 14, 4093–4097; (c)
B. R. Stranix, J.-F. Lavallee, G. Sevigny, J. Yelle, V. Perron,
N. LeBerre, D. Herbart and J. J. Wu, Bioorg. Med. Chem.
9 W. Zhang, J. Xie, B. Rao and M. Luo, J. Org. Chem., 2015, 80,
3504–3511.
Lett., 2006, 16, 3459–3462; (d) Z. H. Chohan, 10 (a) Y. Iwasawa, Tailored Metal Catalysis, Reidel D. Publishing
M. H. Youssou, A. Jarrahpour and T. B. Hadda, Eur. J.
Med. Chem., 2010, 45, 1189–1199; (e) M. Basanagouda,
Company, Dordrecht, Holland, 1986; (b) Y. Yang and
R. M. Rioux, Chem. Commun., 2011, 47, 6557–6559.
K. Shivashankar, M. V. Kulkarni, V. P. Rasal, H. Patel, 11 (a) G. C. H. Chiang and T. Olsson, Org. Lett., 2004, 6, 3079–
S. S. Mutha and A. A. Mohite, Eur. J. Med. Chem., 2010, 45,
1151–1157.
3 (a) D. J. Snodin, Org. Process Res. Dev., 2010, 14, 960–976; (b)
D. A. Pierson, B. A. Olsen, D. K. Robbins, K. M. DeVries and
D. L. Varie, Org. Process Res. Dev., 2009, 13, 285–291; (c)
3082; (b) C. Girard, E. Onen, M. Aufort, S. Beauviere,
E. Samson and J. Herscovici, Org. Lett., 2006, 8, 1689–1692;
(c) J. Yang, P. Li and L. Wang, Tetrahedron, 2011, 67, 5543–
5549; (d) E. Qzkai, S. Ozcubukcu, C. Jimeno and
M. A. Pericas, Catal. Sci. Technol., 2012, 2, 195–200.
P. L. Skipper, M. Y. Kim, H. L. Sun, N. Wogan and 12 (a) S. Benyahya, F. Monnier, M. Taillefer, M. Wong Chi Man,
S. R. Tannenbaum, Carcinogenesis, 2010, 31, 50–58.
4 (a) J. Yin and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124,
6043–6048; (b) J. Baffoe, M. Y. Hoe and B. B. Toure, Org.
Lett., 2010, 12, 1532–1535; (c) B. R. Rosen, J. C. Ruble,
T. J. Beauchamp and A. Navarro, Org. Lett., 2011, 13, 2564–
2567; (d) B. Y.-H. Tan, Y.-C. Teo and A.-H. Seow, Eur. J. Org.
Chem., 2014, 1541–1546.
C. Bied and F. Ouazzani, Adv. Synth. Catal., 2008, 350, 2205–
2208; (b) S. Benyahya, F. Monnier, M. Wong Chi Man,
C. Bied, F. Ouazzani and M. Taillefer, Green Chem., 2009,
11, 1121–1123; (c) A. Coelho, P. Diz, O. Caamano and
E. Sotelo, Adv. Synth. Catal., 2010, 352, 1179–1192; (d)
T. Miao and L. Wang, Synthesis, 2008, 363–368; (e)
L. Zhang, P. Li and L. Wang, Lett. Org. Chem., 2006, 3, 282–
285.
5 (a) P. Y. S. Lam, G. Vincent, C. G. Clark, S. Deudon and
P. K. Jadhav, Tetrahedron Lett., 2001, 42, 3415–3418; (b) 13 (a) S. Chassaing, M. Kumarraja, A. S. S. Sido, P. Pale and
C. Pan, J. Cheng, H. Wu, J. Ding and M. Liu, Synth.
Commun., 2009, 39, 2082–2092; (c) S.-Y. Moon, J. Nam,
K. Rathwell and W.-S. Kim, Org. Lett., 2014, 16, 338–341;
J. Sommer, Org. Lett., 2007, 9, 883–886; (b) S. Chassaing,
A. S. S. Sido, A. Alix, M. Kumarraja, P. Pale and J. Sommer,
Chem.–Eur. J., 2008, 14, 6713–6721.
(d) K. S. Rao and T.-S. Wu, Tetrahedron, 2012, 68, 7735– 14 H. Sharghi, R. Khalifeh and M. M. Doroodmand, Adv. Synth.
7754; (e) J.-B. Lan, G.-L. Zhang, X.-Q. Yu, J.-S. You, L. Chen,
Catal., 2009, 351, 207–218.
M. Yan and R.-G. Xie, Synlett, 2004, 1095–1097; (f) 15 B. H. Lipshutz and B. R. Ta, Angew. Chem., Int. Ed., 2006, 45,
M. L. Kantam, B. Neelima, C. V. Reddy and V. Neeraja, J.
Mol. Catal. A: Chem., 2006, 249, 201–206.
6 (a) H. Qin, N. Yamagiwa, S. Matsunaga and M. Shibasaki,
Angew. Chem., Int. Ed., 2007, 46, 409–413; (b) F. Shi,
8235–8238.
16 H. Sharghi, M. H. Beyzavi, A. Safavi, M. M. Doroodmand and
R. Khalifeh, Adv. Synth. Catal., 2009, 351, 2391–2410.
This journal is © The Royal Society of Chemistry 2016
RSC Adv., 2016, 6, 43605–43612 | 43611