Int. Ed., 43 (2004) 550-556; (c) M. M. Khodaei, E. Nazari,
Tetrahedron Lett., 53 (2012) 5131-5135; (d) O. Mendoza, G.
Rossey, L. Ghosez, Tetrahedron Lett., 52 (2011) 2235-2239; (e) K.
Tangdenpaisala, W. Phakhodeec, S. Ruchirawata, P. Ploypraditha,
Tetrahedron, 69 (2013) 933-941.
good reactivity to afford the desired products 15a-15d in 83%-
85% yields. However, reactions of benzyl alcohol and
cyclohexanol with 5p in the presence of H-mont provided indole-
containing ethers 15e-15f in only 61% and 45% yields,
respectively. In addition, H-mont was found to efficiently
catalyze the reactions of 1,3-dicarbonyl compounds with 5p,
leading to indole-containing β-diketone 16a and β-ketoesters
16b-16c in moderate to good yields (65%-83%).
[3] (a) J. R. Schmink, M. T. Tudge, Tetrahedron Lett., 54 (2013) 15-
20; (b) M. Kuriyama, M. Shinozawa, N. Hamaguchi, S. Matsuo,
O. Onomura, J. Org. Chem., 79 (2014) 5921-5928.
[4] (a) M. A. Schade, A. Metzger, S. Hug and P. Knochel, Chem.
Commun., (2008) 3046-3048; (b) G. Manolikakes, C. M.
Hernandez, M. A. Schade, A. Metzger, P. Knochel, J. Org. Chem.,
73 (2008) 8422-8436.
3. Conclusions
In summary, we have conducted a detailed characterization of
H-mont using different sophisticated analytical instruments, and
developed an efficient synthesis of heterocycle-containing
diarylmethanes through H-mont-mediated Friedel-Crafts-like
alkylation of (hetero)arenes by heterobenzyl acetates under mild
conditions. This protocol has been successfully applied for the
gram-scale synthesis of indole-containing diarylmethane 13 in
good yield for the preparation of Zafirlukast (1). H-mont can also
be applied to the nucleophilic substitution reactions of
heterobenzyl acetate 5p with a variety of alcohols and 1,3-
dicarbonyl compounds. Further utilizations of H-mont-based
catalytic strategy are underway to construct more complex
molecules.
[5] (a) M. F. Enamorado, P. W. Ondachi, D. L. Comins, Org. Lett., 12
(2010) 4513-4515; (b) A. López-Pérez, J. Adrio, J. C. Carretero,
Org. Lett., 11 (2009) 5514-5517.
[6] X. Li, Y. Feng, L. Lin, G. Zou, J. Org. Chem., 77 (2012) 10991-
10995.
[7] (a) K. Motokura, S. Matsunaga, H. Noda, A. Miyaji, T. Baba, ACS
Catal., 2 (2012) 1942-1946; (b) K. Motokura, T. Baba, Green
Chem., 14 (2012) 565-579; (c) K. Motokura, S. Matsunaga, A.
Miyaji, Y. Sakamoto, T. Baba, Org. Lett., 12 (2010) 1508-1511;
(d) K. Motokura, H. Yoneda, A. Miyaji, Y. Sakamotoa, T. Baba,
Catal. Sci. Technol., 1 (2011) 470-479.
[8] K. Motokura, N. Nakagiri, T. Mizugaki, K. Ebitani, K. Kaneda, J.
Org. Chem., 72 (2007) 6006-6015.
[9] (a) K. Motokura, N. Fujita, K. Mori, T. Mizugaki, K. Ebitani, K.
Kaneda, Angew. Chem. Int. Ed., 45 (2006) 2605-2609; (b) K.
Motokura, N. Nakagiri, K. Mori, T. Mizugaki, K. Ebitani, K.
Jitsukawa, K. Kaneda, Org. Lett., 8 (2006) 4617-4620.
Acknowledgments
This work was supported by the National Natural Science
Foundation of China (No. 81602957), and the Open Project of
State Key Laboratory of Natural Medicines (No.
SKLNMKF202012).
[10] (a) A. Harrane, R. Meghabar, M. Belbachir, React. Funct. Polym.,
66 (2006) 1696-1702; (b) M. I. Ferrahi, M. Belbachir, Molecules, 9
(2004) 968-977; (c) Z. Maeno, S. Yamada, T. Mitsudome, T.
Mizugaki, K. Jitsukawa, Green Chem., 19 (2017) 2612-2619.
[11] D. Chen, P. Zhang, Y. Sun, P. Wang, C. Zhang, L. Kong, J. Zhang,
H. Sun, X. Wen, Org. Biomol. Chem., 14 (2016) 11154-11161.
[12] D. Chen, C. Xu, J. Deng, C. Jiang, X. Wen, L. Kong, J. Zhang, H.
Sun, Tetrahedron, 70 (2014) 1975-1983.
References and notes
[1] For selected papers, see: (a) S. Suissa, R. Dennis, P. Ernst, O.
Sheehy, S. Wood-Dauphinee, Ann. Intern. Med., 126 (1997) 177-
183; (b) A. J. Scheen, Drugs, 75 (2015) 33-59; (c) M. S. Lara, W.
S. Holland, D. Chinn, R. A. Burich, P. N. Jr Lara, D. R. Gandara,
K. Kelly, P. C. Mack, Clin. Lung Cancer, 18 (2017) 281-285; (d)
Antibiot (Tokyo), 73 (2020) 5-27.
[13] (a) P. J. Wallis, W. P. Gates, A. F. Patti, J. L. Scott, E. Teoha,
Green Chem., 9 (2007) 980-986; (b) K. Kaneda, Synlett, (2007)
999-1015.
[14] (a) V. G. Matassa, T. P. Jr Maduskuie, H. S. Shapiro, B. Hesp, D.
W. Snyder, D. Aharony, R. D. Krell, R. A. Keith, J. Med. Chem.,
33 (1990) 1781-1790; (b) C. L. Ancell, I. Derrick, J. D. Moseley,
J. A. Stott, Org. Process Res. Dev., 8 (2004) 808-813.
[2] (a) G. A. Olah, Friedel–Crafts Chemistry, Wiley, New York,
(1973); (b) M. Bandini, A. Melloni, A. U. Ronchi, Angew. Chem.