Page 5 of 6
RSC Advances
DOI: 10.1039/C5RA03462K
8. S. K. Sahoo, A. Banerjee, S. Chakraborty and B. K. Patel, ACS Catal.,
2012, 2, 544.
9. Q. Zhang, F. Yang and Y. Wu, Chem. Commun., 2013, 49, 6837.
70 10. Y.-J. Bian, C.-B. Xiang, Z.-M. Chen and Z.-Z. Huang, Synlett, 2011,
2407.
A oven-dried round bottle flask was charged with 2-
phenylpyridine (1), (0.5 mmol, 0.078 g), benzyl ether (a) (0.75
mmol, 0.149 g), Cu(OAc)2 (20 mol%, 0.018 g), 70% aqueous
solution TBHP (6 equiv., 430 µL) in chlorobenzene (0.5 mL).
This resultant reaction mixture was stirred in a preheated oil bath
at 120 oC for 22 h and the progress of the reaction was monitored
by TLC. The reaction mixture was cooled down to room
temperature, residual solvent evaporated under reduced pressure
and diluted with ethyl acetate (1 x 10 mL). This diluted reaction
5
11. (a) D. Kalyani and M. S. Sanford, Org. Lett., 2005, 7, 4149; (b) F.-R.
Gou, X.-C. Wang, P.-F. Huo, H.-P. Bi, Z.-H. Guan and Y.-M. Liang, Org.
Lett., 2009, 11, 5726; (c) X. Zheng, B. Song and B. Xu, Eur. J. Org.
75 Chem., 2010, 4376; (d) L. Wang, X.-D. Xia, W. Guo, J.-R. Chen and W.-
J. Xiao, Org. Biomol. Chem., 2011, 9, 6895; (e) R. K. Rit, R. Yadav and
A. K. Sahoo, Org. Lett., 2012, 14, 3724; (f) R. Yadav, R. K. Rit and A. K.
Sahoo, Chem.-Eur. J., 2012, 18, 5541.
12. (a) X. Chen, X.-S. Hao, C. E. Goodhue and J.-Q. Yu, J. Am. Chem.
80 Soc., 2006, 128, 6790; (b) S. H. Kim, H. S. Lee, S. H. Kim and J. N. Kim,
Tetrahedron Lett., 2008, 49, 5863; (c) A. Company and S. Enthaler,
Chem. Soc. Rev., 2011, 40, 4912; (d) D. A. Alonso, C. Najera, I. M.
Pastor and M. Yus, Chem.-Eur. J., 2010, 16, 5274; (e) V. S.
Thirunavukkarasu, S. I. Kozhushkov and L. Ackermann, Chem.
85 Commun., 2014, 50, 29.
10 mixture was passed through a celite bed and subsequently washed
with ethyl acetate (2 x 10 mL). The combined organic layer was
then washed with 10% aq. saturated solution of NaHCO3 (2 x 5
mL) followed by water (2 x 5 mL). The organic layer was dried
over anhydrous Na2SO4 and evaporated under reduced pressure.
15 The crude product was further purified by silica gel column
chromatography using (heane : ethylacetate:: 9 : 1) as the eluent
to give pure compound (2-(pyridin-2-yl)phenyl benzoate) (1a,
0.08 g, 58%) as a brownish oil material.
13. F. Luo, C. Pan and J. Cheng, Synlett, 2012, 23, 357.
14. A. R. Dick, J. W. Kampf and M. S. Sanford, J. Am. Chem. Soc., 2005,
127, 12790.
15. (a) C.-L. Sun, J. Liu, Y. Wang, X. Zhou, B.-J. Li and Z.-J. Shi,
90 Synlett, 2011, 22, 883; (b) C.-J. Hu, X.-H. Zhang, Q.-P. Ding, T. Lv, S.-P.
Ge and P. Zhong, Tetrahedron Lett., 2012, 53, 2465; (c) W.-N. Sit, C.-W.
Chan and W.-Y. Yu, Molecules, 2013, 18, 4403, (d) S. K. Santra, A.
Banerjee, N. Khatun and B. K. Patel, Eur. J. Org. Chem., 2015, 350 and
references therein.
95 16. (a) Z. Ye, W. Wang, F. Luo, S. Zhang and J. Cheng, Org. Lett., 2009,
11, 3974; (b) K. Padala and M. Jeganmohan, Chem. Commun., 2013, 49,
9651.
Acknowledgement
20 B. K. P acknowledges the support of this research by the Science
and Engineering Research Board (SERB) (SB/S1/OC-53/2013),
New Delhi, and the Council of Scientific and Industrial Research
(CSIR) (02(0096)/12/EMR-II). N.K. A.B. S.K.S. and W.A thank
CSIR.
25
References
17. (a) W. Wang, F. Luo, S. Zhang and J. Cheng, J. Org. Chem., 2010,
75, 2415; (b) W. Wang, C. Pan, F. Chen and J. Cheng, Chem. Commun.,
100 2011, 47, 3978.
18. A. B. Khemnar and B. M. Bhanage, Org. Biomol. Chem., 2014, 12,
9631.
19. (a) K. Padala and M. Jeganmohan, Chem. Commun., 2013, 49, 9651;
(b) K. Padala and M. Jeganmohan, Chem.–Eur. J., 2014, 20, 4092; (c) C.-
105 L. Sun, J. Liu, Y. Wang, X. Zhou, B.-J. Li and Z.-J. Shi, Synlett, 2011,
883.
1. (a) G. Dyker, Handbook of C–H Transformations: Applications in
Organic Synthesis, Wiley-VCH, Weinheim, 2005; (b) J.-Q. Yu and Z.-J.
Shi, C–H Activation, Springer, Berlin, Germany, 2010; (c) X. Chen, K.
30 M. Engle, D.-H. Wang and J.-Q. Yu, Angew. Chem. Int. Ed., 2009, 48,
5094; (d) T. Satoh and M. Miura, Chem.–Eur. J., 2010, 16, 11212; (e) T.
W. Lyons and M. S. Sanford, Chem. Rev., 2010, 110, 1147; (f) L.-M. Xu,
B.-J. Li, Z. Yang and Z.-J. Shi, Chem. Soc. Rev., 2010, 39, 712; (g) D. A.
Colby, R. G. Bergman and J. A. Ellman, Chem. Rev., 2010, 110, 624; (h)
35 J. Wencel-Delord, T. Droge, F. Liu and F. Glorius, Chem. Soc. Rev.,
2011, 40, 4740; (i) S. H. Cho, J. Y. Kim, J. Kwak and S. Chang, Chem.
Soc. Rev., 2011, 40, 5068; (j) C.-L. Sun, B.-J. Li and Z.-J. Shi, Chem.
Rev., 2011, 111, 1293; (k) L. Ackermann, Chem. Rev., 2011, 111, 1315;
(l) S. E. Allen, R. R. Walvoord, R. Padilla-Salinas and M. C. Kozlowski,
40 Chem. Rev., 2013, 113, 6234.
20. (a) C. J. Li, Acc. Chem. Res., 2009, 42, 335; (b) Z. Li, D. S. Bohle,
and C.-J. Li, Proc. Natl. Acad. Sci., 103, 8928.
21. A. E. King, L. M. Huffman, A. Casitas, M. Costas, X. Ribas and S. S.
110 stahl, J. Am. Chem. Soc., 2010, 132, 12068.
2. (a) S. K. Rout, S. Guin, K. K. Ghara, A. Banerjee and B. K. Patel, Org.
Lett., 2012, 14, 3982; (b) S. Guin, S. K. Rout, A. Banerjee, S. Nandi and
B. K. Patel, Org. Lett., 2012, 14, 5294; (c) S. K. Rout, S. Guin, A.
Banerjee, N. Khatun, A. Gogoi and B. K. Patel, Org. Lett., 2013, 15,
45 4106; (d) G. Majji, S. Guin, A. Gogoi, S. K. Rout and B. K. Patel, Chem.
Commun., 2013, 49, 3031.
3. (a) S. K. Rout, S. Guin, A. Gogoi, G. Majji and B. K. Patel, Org. Lett.,
2014, 16, 1614; (b) G. Majji, S. Guin, S. K. Rout, A. Behera and B. K.
Patel, Chem. Commun., 2014, 50, 12193; (c) N. Khatun, A. Banerjee, S.
50 K. Santra, A. Behera and B. K. Patel, RSC Adv., 2014, 4, 54532.
4. A. Behera, S. K. Rout, S. Guin and B. K. Patel, RSC Adv., 2014, 4,
55115.
5. P. G. M. Wuts and T. W. Green, Protective Groups in Organic
Synthesis, 4th ed.; Wiley & Sons: New York, 2007, pp 102.
55 6. (a) D. G. Markees, J. Org. Chem., 1958, 23, 1490; (b) A. S. Mayhoub,
A. Talukdar and M. Cushman, J. Org. Chem., 2010, 75, 3507; (c) P. P.
Pradhan, J. M. Bobbitt and W. F. Bailey, J. Org. Chem., 2009, 74, 9524;
(d) P. Strazzolini and A. Runcio, Eur. J. Org. Chem., 2003, 526; (e) T.
Nishiguchi and M. Bougauchi, J. Org. Chem., 1989, 54, 3001; (f) E. Lee-
60 Ruff and F.Ablenas, J. Can. J. Chem., 1989, 67, 699; (g) Z. Shen, J. Dai,
J. Xiong, X. He, W. Mo, B. Hu, N. Sun and X. Hu, Adv. Synth. Catal.,
2011, 353, 3031.
7. (a) S. Han, S. Sharma, J. Park, M. Kim, Y. Shin, N. K. Mishra, J. J.
Bae, J. H. Kwak, Y. H. Jung and I. S. Kim, J. Org. Chem., 2014, 79, 275;
65 (b) J. Park, S. H. Han, S. Sharma, S. Han, Y. Shin, N. K. Mishra, J. H.
Kwak, C. H. Lee, J. Lee and I. S. Kim, J. Org. Chem., 2014, 79, 4735.
This journal is © The Royal Society of Chemistry [year]
Journal Name, [year], [vol], 00–00 | 5