10.1002/adsc.201700125
Advanced Synthesis & Catalysis
B. E. Maki, A. Chan, E. M. Phillips and K. A.
Scheidt, Tetrahedron, 2009, 65, 3102-3109; e) S. D.
Sarkar, S. Grimme and A. Studer, J. Am. Chem. Soc.,
2010, 132, 1190-1191; f) C. A. Rose and K. Zeitler,
Org. Lett., 2010, 12, 4552-4555; g) B. Maji, S.
Vedachalan, X. Ge, S. Cai and X.-W. Liu, J. Org.
Chem., 2011, 76, 3016-3023; h) E. E. Finney, K. A.
scope of the reaction includes heterocyclic ketone, 2-
acetyl naphthalene, sterically hindered 2-substituted
acetophenone
and
various
substituted
2-
aminopyridines.
Experimental Section
General procedure
Ogawa and A. J. Boydston, J. Am. Chem. Soc., 2012
,
134, 12374-12377; i) P. Arde, B. T. Ramanjaneyulu,
V. Reddy, A. Saxena and R. V. Anand, Org. Biomol.
Chem., 2012, 10, 848-851; j) T. Uno, T. Inokuma and
Y. Takemoto, Chem. Commun., 2012, 48, 1901-1903;
k) J. Zhao, C. Mück-Lichtenfeld and A. Studer, Adv.
Synth. Catal., 2013, 355, 1098-1106.
A mixture of NHC-precursor A (0.1 mmol) and Et3N (0.1
o
mmol) in DMF (1 mL) was stirred at 25 C for 30 min. To
this solution, acetophenone (1.0 mmol), 2-aminopyridine
and SnCl2·2H2O (0.1 mmol) was added followed by 70%
TBHP in H2O (3.0 mmol) and stirring was continued at 120
oC for 20 h. Progress of the reaction was monitored by TLC.
After the completion of the reaction, the mixture was
washed with plenty of water and extracted with ethyl acetate.
The extract was washed with brine solution and dried over
anhydrous Na2SO4. Removal of the solvent under vacuum
afforded the crude product, which was purified by column
chromatography using hexane/ethyl acetate mixture.
[8] a) V. Nair, V. Varghese, R. R. Paul, A. Jose, C. R.
Sinu and R. S. Menon, Org. Lett., 2010, 12, 2653-
2656; b) P.-C. Chian and J. W. Bode, Org. Lett.,
2011, 13, 2422-2425.
[9] a) B. E. Maki, A. Chan, E. M. Phillips and K. A.
Scheidt, Org. Lett., 2007, 9, 371-374; b) D.- F. Yu, P.
Xing and B. Jiang, Tetrahedron, 2015, 71, 4269-
4273.
Acknowledgements
C. U thanks DST, SERB, New Delhi for the award of a research
grant for young scientist (no. SB/FT/CS-108/2012), New Delhi.
[10] For NHC catalyzed oxidative amidations: a) J. W.
Bode and S. S. Sohn, J. Am. Chem. Soc., 2007, 129,
13798-13799; b) H. U. Vora and T. Rovis, J. Am.
Chem. Soc., 2007, 129, 13796-13797; c) F. T. Wong,
P. K. Patra, J. Seayad, Y. Zhang and J. Y. Ying, Org.
Lett., 2008, 10, 2333-2336; d) S. D. Sarkar and A.
Studer, Org. Lett., 2010, 12, 1992-1995.
References
[1] a) S. Kobayashi and H. Ishitani, Chem. Rev., 1999
,
99, 1069-1094; b) M. Benaglia, M. Cinquini and F.
Cozzi, Eur. J. Org. Chem., 2000, 563-572; c) A.
Córdova, Acc. Chem. Res., 2004, 37, 102-112; d) M.
M. B. Marques, Angew. Chem., Int. Ed., 2006, 45,
348-352 and references cited therein.
[11] a) A. Anitha and C. U. Maheswari, Adv. Synth.
Catal., 2015, 357, 1199-1203; b) A. Anitha, E. S.
Devi, S. Nagarajan, V. Sridharan, A. Suvitha and C.
U. Maheswari, Eur. J. Org. Chem., 2016, 2016, 4872-
4880.
[2] a) F. F. Blicke, Org. React., 1942, 1, 303-341; b) M.
Arend, B. Westerman and N. Risch, Angew. Chem.,
Int. Ed., 1998, 37, 1044-1070; c) K. Manabe, Y. Mori
and S. Kobayashi, Tetrahedron, 2001, 57, 2537-2544;
d) T. Muraoka, S. Kamiya, S. I. Matsuda and K. Itoh,
Chem. Commun., 2003, 449-460; e) B. M. Trost and
L. R. Terrell, J. Am. Chem. Soc., 2003, 125, 338-339;
f) N. B. Ambhaikar, J. P. Snyder and D. C. Liotta, J.
Am. Chem. Soc., 2003, 125, 3690-3691; g) S.
Kobayashi, R. Matsubara, Y. Nakamura, H. Kitagawa
and M. Sugiura, J. Am. Chem. Soc., 2003, 125, 2507-
2515.
[12] a) S. Ding and N. Jiao, Angew. Chem., Int. Ed.,
2012, 51, 9226-9237; b) J. Muzart, Tetrahedron,
2009, 65, 8313-8323.
[13] a) S. Ding and N. Jiao, J. Am. Chem. Soc., 2011
,
133, 12374-12377; b) G. Zhang, X. Ren, J. Chen, M.
Hu and J. Cheng, Org. Lett., 2011, 13, 5004-5007; c)
G. Ishii, K. Moriyama and H. Togo, Tetrahedron
Lett., 2011, 52, 2404-2406; d) A. Sharma, V. P.
Mehta and E. V. Eychen, Tetrahedron, 2008, 64,
2605-2611; e) J. Wang, J. T. Hou, J. Wen, J. Zhang
and X.-Q. Yu, Chem. Commun., 2011, 47, 3652-
3654; f) Y. Li, Y. Xie, R. Zhang, K. Jin, X. Wang and
C. Duan, J. Org. Chem., 2011, 76, 5444-5449; g) ) M.
A. Suchy, A. H. Elmehriki and R. H. E. Hudson, Org.
Lett., 2011, 13, 3952-3955.
[3] a) D. J. Dixon and R. D. Richardson, Synlett, 2005
,
81-85; b) M. Terada, K. Machioka and K. Sorimachi,
Angew. Chem., Int. Ed., 2006, 45, 2254-2257; c) S. J.
Connon, Angew. Chem., Int. Ed., 2006, 45, 3909-
3912.
[14] a) Y. Li, D. Xue, W. Lu, C. Wang, Z.-T. Liu and J.
Xiao, Org. Lett., 2014, 16, 66-69; b) A. Borah, L.
Goswami, K. Neog and P. Gogoi, J. Org. Chem.,
2015, 80, 4722-4728; c) F. Pu, Y. Li, Y.-H. Song, J.
Xiao, Z.-W. Liu, C. Wang, Z.-T. Liu, J.-G. Chen and
J. Lu, Adv. Synth. Catal., 2016, 358, 539-542; d) S.
Mondal, S. Samanta, S. Santra, A. K. Bagdi and A.
Hajra, Adv. Synth. Catal., 2016, 358, 3633-3641; e) J.
Liu, H. Yi, X. Zhang, C. Liu, R. Liu, G. Zhang and A.
Lei, Chem. Commun., 2014, 50, 7636-7638.
[4] Y. Nakamura, R. Matsubara, H. Kiyohara and S.
Kobayashi, Org. Lett., 2003, 5, 2481-2484.
[5] E. F. Kleinman, in Comprehensive Organic
Synthesis, ed. B. M. Trost, Pergamon, Oxford, 1991
Vol. 2, pp. 893.
,
[6] a) W. Notz, K. Sakthivel, T. Bui, G. Zhong and C. F.
Barbas, III, Tetrahedron Lett., 2001, 42, 199-201; b)
B. List, P. Pojarliev, W. T. Biller and H. J. Martin, J.
Am. Chem. Soc., 2002, 124, 827-833; c) M. Benaglia,
M. Cinquini, F. Cozzi, A. Puglisi and G. Celentano,
Adv. Synth. Catal., 2002, 344, 533-542.
[15] CCDC 1528059, contain the supplementary
crystallographic data for this paper. These data can be
obtained free of charge from The Cambridge
Crystallographic
Data
Centre
via
[7] a) J. Guin, S. D. Sarkar, S. Grimme and A. Studer,
Angew. Chem., Int. Ed., 2008, 47, 8727-8730; b) B.
E. Maki and K. A. Scheidt, Org. Lett., 2008, 10,
4331-4334; c) C. Noonan, L. Baragwanath and S. J.
Cannon, Tetrahedron Lett., 2008, 49, 4003-4006; d)
[16] D. Lim, F. Fang, G. Zhou and D. M. Coltart, Org.
Lett., 2007, 9, 4139-4142 and references cited therein.
5
This article is protected by copyright. All rights reserved.