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Organic & Biomolecular Chemistry
Page 4 of 4
DOI: 10.1039/C5OB02535D
COMMUNICATION
Journal Name
1
(a) T. Sugahara, K. Murakami, H. Yorimitsu and A. Osuka,
10 (a) M. Arisawa, T. Suzuki, T. Ishikawa, M. Yamaguchi, J. Am.
Chem. Soc., 2008, 130, 12214; (b) J.-H. Cheng, C.L. Yi, T.-J. Liu,
C.-F. Le, Chem. Commun., 2012, 48, 8440; (c) S. Singh, L. D. S.
Yadav, Org. Biomol. Chem., 2012, 10, 3932; (d) J.-C. Zhao, H.
Fang, J.-L. Han, Y. Pan, G. Li, Adv. Synth. Catal., 2014, 356,
2719; (e) D. Kundu, S. Ahammed, B. C. Ranu, Green Chem.,
2012, 14, 2024.
Angew. Chem. Int. Ed., 2014, 53, 9329; (b) L. Rout, S. Jammi
and T. Punniyamurthy, Org. Lett., 2007, 9, 3397; (c) B. P. Fors
and S. L. Buchwald, J. Am. Chem. Soc., 2010, 132, 15914; (d) F.
Perez and A. Minatti, Org. Lett., 2011, 13, 1984.
2
(a) Y. T. Han, G. I. Choi, D. Son, N. J. Kim, H. Yun, S. Lee, D. J.
Chang, H. S. Hong, H. Kim, H. J. Ha, Y. H. Kim, H. J. Park, J. Lee
and Y. G. Suh, J. Med. Chem., 2012, 55, 9120; (b) K. Singh, H.
Kaur, K. Chibale, J. Balzarini, S. Little and P. V. Bharatam, Eur. J.
Med. Chem., 2012, 52, 82; (c) K. Singh, K. Singh, B. Wan, S.
Franzblau, K. Chibale and J. Balzarini, Eur. J. Med. Chem.,
2011, 46, 2290; (d) Z.-Q. Liu, S.-T. Zhuo, J.-H. Tan, T.-M. Ou, D.
Li, L.-Q. Gu and Z.-S. Huang, Tetrahedron, 2013, 69, 4922.
(a) J. P. Wolfe and S. L. Buchwald, Angew. Chem. Int. Ed., 1999,
38, 2413; (b) B. Schlummer and U. Scholz, Adv. Synth. Catal.,
2004, 346, 1599; (c) S. Surry and S. L. Buchwald, Angew.
Chem. Int. Ed., 2008, 47, 6338; (d) Monnier, and M. Taillefer,
Angew. Chem. Int. Ed., 2009, 48, 6954; (e) V. Kumar, K. Kaur, G.
K. Gupta and A. K. Sharma, Eur J Med. Chem, 2013, 69, 735.
(a) J. Jiao, X. R. Zhang, N. H. Chang, J. Wang, J. F. Wei, X. Y. Shi
and Z. G. Chen, J. Org Chem., 2011, 76, 1180.
11 (a) B. C. Ranu and T. Mandal, J. Org. Chem., 2004, 69, 5793. (b)
N. Taniguchi, J. Org. Chem., 2004, 69, 6904. (c) S. Kumar and L.
Engman, J. Org. Chem., 2006, 71, 5400.
12 (a) A. Kumar and S. Kumar, Tetrahedron, 2014, 70, 1763; (b) S.
Saba, J. Rafique and A. L. Braga, Adv. Synth. Catal., 2015, 357,
1446; (c) Y. Guo, Z.-J. Quan, Y.-X. Da, Z. Zhang and X.-C. Wang,
RSC Adv., 2015, 5, 45479.
3
13 H. Y. Tu, B. L. Hu, C. L. Deng and X. G. Zhang, Chem. Commun.,
2015, 51, 15558.
14 C. Cai, M.-j. Bu and G.-p. Lu, Synlett, 2015, 26, 1841.
15 Z.-J. Quan, Y. Lv, F.-Q. Jing, X.-D. Jia, C.-D. Huo and X.-C. Wang,
Adv. Synth. Catal., 2014, 356, 325.
16 B.-X. Du, Z.-J. Quan, Y.-X. Da, Z. Zhang and X.-C. Wang, Adv.
Synth. Catal., 2015, 357, 1270.
4
5
17 M. Matloobi and C. O. Kappe, ACS. Comb. Sci. 2007, 9,275.
18 (a) X.-C. Wang, G.-J. Yang, Z.-J. Quan, P.-Y. Ji, J.-L. Liang and R.-
G. Ren, Synlett, 2010, 11, 1657; (b) Z.-J. Quan, F.-Q. Jing, Z.
Zhang, Y.-X. Da and X.-C. Wang, Eur. J. Org. Chem., 2013, 31,
7175. (c) Y. Zhang, Z.-J. Quan, H.-P. Gong, Y.-X. Da, Z. Zhang
and X.-C. Wang, Tetrahedron, 2015, 71, 2113; (d) T. Xing, K.-J.
Wei, Z.-J. Quan and X.-C. Wang, Synthesis, 2015, 47, 3925.
19 Procedures for the synthesis of unsymmetrical disulfides 6a
and 6b: the mixture of ethyl 6-methyl-4-aryl-2-thioxo-1,2,3,4-
tetrahydropyrimidine-5-carboxylate (5 mmol), p-toluenethiol
(5 mmol), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (5
mmol) and NaH (5 mmol) in dioxane (15.0 mL) in 100 mL
round-bottom flask was stirred at rt for 5 min. Then, 2 mL
diluted hydrochloric acid was added to the mixture to quench
the reaction and extracted with ethyl acetate (3×25 mL). The
combined organic layers were washed with aqueous NaHCO3
and brine, dried over MgSO4, filtered, and the volatiles were
removed in vacuo. The residue was purified by column
chromatography on silica gel (ethyl acetate/ petroleum ether
1:10) to give the product.
(a) A. T. Brusoe and J. F. Hartwig, J Am Chem Soc., 2015, 137,
8460; (b) A. Chartoire, M. Lesieur, A. M. Z. Slawin, S. P. Nolan
and C. S. J. Cazin, Organometallics, 2011, 30, 4432. (c) M. A.
McGowan, C. Z. McAvoy, and S. L. Buchwald, Org. Lett., 2012
14, 3800; (d) S. M. Raders, J. N. Moore, J. K. Parks, A. D. Miller,
T. M. Leißing, S. P. Kelley, R. D. Rogers and K. H. Shaughnessy,
J. Org. Chem., 2013, 78, 4649.
6
7
(a) C. Bolm, J. Hildebr and J. Rudolph, Synthesis, 2000, 2000,
911; (b) C.-Y. Gao, L.-M. Yang, J. Org. Chem., 2008, 73, 1624.
(a) D.-W. Ma, Q. Cai and H. Zhang, Org. Lett., 2003, 5, 2453; (b)
D. Guo, H. Huang, J. Xu, H. Jiang and H. Liu, Org. Lett., 2008,
10, 4513; (c) G. A. Molander, C. S. Yun, M. Ribagoroa, B.
Biolatto, J. Org. Chem., 2003, 68, 5534; (d) B. P. Fors, N. R.
Davis and S. L. Buchwald, J. Am. Chem. Soc., 2009, 131, 5766.
(a) K. Dooleweerdt, B. P. Fors and S. L. Buchwald, Org. lett.,
2010, 12, 2350; (b) B. P. Fors, D. A. Watson, M. R. Biscoe and S.
L. Buchwald, J. Am. Chem. Soc., 2008, 130, 13552; (c) C. M. So,
Z. Zhou, C. P. Lau and F. Y. Kwong, Angew Chem Int Ed., 2008,
47, 6402; (d) G. D. Vo and J. F. Hartwig, J. Am. Chem. Soc.,
2009, 131, 11049.
8
9
20 N. Taniguchi, J. Org. Chem. 2007, 72, 1241.
21 Z.-J. Quan, Y. Lv, Z.-J. Wang, Z. Zhang, Y.-X.Da, X.-C. Wang,
Tetrahedron Lett., 2013, 54, 1884.
(a) P. D. B. de La Mare, Electrophilic Halogenation, Cambridge
University Press, New York, 1976; (b) H. H. Hodgson, Chem.
Rev., 1947, 40, 251.
4 | J. Name., 2012, 00, 1-3
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