Full Papers
Chem. Eur. J. 2014, 20, 3903–3907; d) D. Hueber, M. Hoffmann, P.
De Frémont, P. Pale, A. Blanc, Organometallics 2015, 34, 5065–5072; e) F.
Sirindil, S. P. Nolan, S. Dagorne, P. Pale, A. Blanc, P. de Frémont, Chem.
Eur. J. 2018, 24, 12630-12637.
Acknowledgements
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The authors thank the CNRS, the French Ministry of Research and
the Russian Science Foundation (grant no. 18-13-00008). OZ
thanks the Russian Science Foundation for a PhD fellowship.
[18] For selected exemples with protic-zeolites, see: a) S. Chassaing, M.
Kumarraja, P. Pale, J. Sommer, Org. Lett. 2007, 9, 3889–3892; b) G.
Mendonca, A. Bastos, M. Boltz, B. Louis, P. Esteves, P. Pale, M. De Mattos,
Appl. Catal. A 2013, 450, 46–51; c) P. Losch, A.-S. Felten, P. Pale Adv. Cat.
Synth. 2015, 357, 2931–2938; For selected exemples with metalated-
zeolites, see: d) S. Chassaing, A. Alix, T. Boningari, A. Sani Souna Sido, M.
Keller, P. Kuhn, B. Louis, P. Pale, J. Sommer, Synthesis 2010, 1557–1567;
e) H. Harkat, S. Borghèse, M. De Nigris, S. Kiselev, V. Bénéteau, P. Pale,
Adv. Synth. Catal. 2014, 356, 3842–3848; f) V. Magné, T. Garnier, M.
Danel, P. Pale, S. Chassaing, Org. Lett. 2015, 17, 4494.
Conflict of Interest
The authors declare no conflict of interest.
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50
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52
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56
57
[19] A. Sani-Souna-Sido, S. Chassaing, P. Pale, J. Sommer, Appl. Catal. A 2008,
336, 101–108.
Keywords: coumarin · thiocoumarin · zeolite · cyclization
[20] For the detection of dicationic species in superacid media, see: a) A.
Vasilyev, S. Walspurger, M. Haouas, P. Pale, J. Sommer, A. P. Rudenko,
Org. Biomol. Chem. 2004, 2, 3483–3489; b) A. Vasilyev, S. Walspurger, J.
Sommer, P. Pale, Tetrahedron 2005, 61, 3559–3564.
[21] G. A. Olah, D. A. Klumpp, Superelectrophiles and their Chemistry, Wiley,
New York, 2008.
[22] a) B. Louis, S. Walspurger, J. Sommer, Catal. Lett. 2004, 93, 81–84; b) B.
Louis, A. Vicente, C. Fernandez, V. Valtchev, J. Phys. Chem. C. 2011, 115,
18603–18610.
[1] A. Estévez-Braun, A. G. Gonzalez, Nat. Prod. Rep. 1997, 14, 465–475.
[2] D. A. Olmedo, J. L. López-Pérez, E. del Olmo, L. M. Bedoya, R. Sancho, J.
Alcamí, E. Muñoz, A. San Feliciano, M. P. Gupta, Molecules 2017, 22,
321–334.
[3] A.-F Asai, F. Iinuma, M. Tanaka, T. Takenaka, M. Mizuno, Phytochemistry
1991, 30, 3091–3093.
[4] a) A. Stefanachi, F. Leonetti, L. Pisani, M. Catto, A. Carotti, Molecules
2018, 23, 250-x; b) S. Emami, S. Dadashpour, Eur. J. Med. Chem. 2015,
102, 611–630; c) K. N. Venugopala, V. Rashmi, B. Odhav, BioMed Res. Int.
2013, 2013, ID 963248, (https://doi.org/10.1155/2013/963248); d) F.
Borges, F. Roleira, N. Milhazes, L. Santana, E. Uriarte, Curr. Med. Chem.
2005, 12, 887–916.
[5] a) H. Y. Song, M. H. Ngai, Z. Y. Song, P. A. MacAry, J. Hobley, M. J. Lear,
Org. Biomol. Chem. 2009, 7, 3400–3406; b) H. S. Jung, P. S. Kwon, J. W.
Lee, J. I. Kim, C. S. Hong, J. W. Kim, S. Yan, J. Y. Lee, J. H. Lee, T. Joo, J. S.
Kim, J. Am. Chem. Soc. 2009, 131, 2008–2012
[6] a) Y. Jing, B. P. Chaplin, Environ. Sci. Technol. 2017, 51, 2355–2365;
b) A. M. Zobel, S. A. Brown, Allelopathy J. 1995, 2, 9–20.
[7] S. R. Trenor, A. R. Shultz, B. J. Love, T. E. Long, Chem. Rev. 2004, 104,
3059–3078.
[8] A. Clayton, W. Godden, J. Chem. Soc. Trans. 1912, 101, 210–216.
[9] A. Maresca, C. Temperini, L. Pochet, B Masereel, A. Scozzafava, C. T.
Supuran, J. Med. Chem. 2010, 53, 335–344.
[10] S. Kumar, B. K. Singh, N. Kalra, V. Kumar, A. Kumar, A. K. Prasad, H. G. Raj,
V. S. Parmar, B. Ghosh, Bioorg. Med. Chem. 2005, 13, 1605–1613.
[11] a) M. G. Choi, Y. H. Kim, J. E. Namgoong, S.-K. Chang, Chem. Commun.
2009, 0, 3560–3562; b) J. E. Park, M. G. Choi, S. K. Chang, Inorg. Chem.
2012, 51, 2880–2884.
[23] A. Vasilyev, S. Walspurger, S. Chassaing, P. Pale, J. Sommer, Eur. J. Org.
Chem. 2007, 5740–5748.
[24] a) E. G. Derouane, J. Catal. 1986, 100, 541–544; b) E. G. Derouane, J. M.
André, A. A. Lucas, Chem. Phys. Lett. 1987, 137, 336–340 ; c) E. G.
Derouane, J. M. André, A. A. Lucas, J. Catal. 1988, 110, 58–73. For a more
recent survey, see: d) G. Sastres, A. Corma, J. Mol. Catal. A 2009, 305, 3–
7; e) R. Gounder, E. Iglesia, Chem. Commun. 2013, 49, 3491–3509.
[25] a) S. Chassaing, M. Kumarraja, P. Pale, J. Sommer, Org. Lett. 2007, 9,
3889–3892; b) C. Bernardon, V. Beneteau, B. Louis, P. Pale, ChemPlu-
sChem 2013, 78, 1134–1141.
[26] C. Mirodatos, D. Barthomeuf, J. Chem. Soc. Chem. Commun. 1981, 39–40
[27] B. Louis, M. M. Pereira, F. M. Santos, P. M. Esteves, J. Sommer, Chem. Eur.
J. 2010, 16, 573–576; P. Mothe-Esteves, B. Louis , J. Phys. Chem. B. 2006,
110, 16793–16800.
[28] a) S. J. De Canio, J. R. Sohn, P. O. Fritz, J. H. Lunsford, J. Catal. 1986, 101,
132–141; b) R. A. Beyerlein, G. B. McVicker, L. N. Yacullo, J. J. Ziemiak, J.
Phys. Chem. 1988, 92, 1967–1970; c) A. Corma, Chem. Rev. 1995, 95,
559–614.
[29] a) J. A. van Bokhoven, M. Tromp, D. C. Koningsberger, J. T. Miller, J. A. Z.
Pieterse, J. A. Lercher, B. A. Williams, H. H. Kung, J. Catal. 2001, 202, 129–
140; b) J. A. van Bokhoven, B. A. Williams, W. Ji, D. C. Koningsberger,
H. H. Kung, J. T. Miller, J. Catal. 2004, 224, 50–59.
[30] Such differences between conversion and yield may be due to the size
of the so-formed coumarins. Indeed, the coumarin calculated molecular
volume seems correlated to the corresponding isolated yields: coumarin
2a with a calculated molecular volume of 228.3 Å3 is recovered more
efficiently (82% isolated yield) than bulkier 2b (244.3 Å3 ; 65% isolated
yield) and 2c (244.4 Å3; 44% isolated yield).
[31] For reactions in which the zeolite catalyst either shifted the reaction
regio- or stereochemistry or force a reaction to proceed, see: a) Y.-Z.
Chen, L.-Z. Wu, L.-P. Zhang, C.-H. Tung, J. Org. Chem. 2005, 70, 4676–
4681; b) Olmos, A. Alix, J. Sommer, P. Pale , Chem. Eur. J. 2009, 15,
11229–11234 ; c) S. Borghese, P. Drouhin, V. Beneteau, B. Louis, P. Pale,
Green Chem. 2013, 15, 1496–1500
[12] a) For recent reviews, see: A. Y. Fedorov, A. V. Nyuchev, I. P. Beletskaya,
Chem. Heterocycl. Compd. 2012, 48, 166–178; b) R. J. Vekariya, H. D.
Patel, Synth. Commun. 2014, 44, 2756–2788; c) F. G. Medina, J. C.
Marrero, M. Macias-Alonso, M. C. Gonzales, I. Cordova-Guerrero, A. G.
Teissier Garcia, S. Osegueda-Robles, Nat. Prod. Rep. 2015, 32, 1472–1507;
d) A. S. Zambare, F. A. Kalam Khan, S. P. Zambare, S. D. Shinde, J. N.
Sangshetti, Curr. Org. Chem. 2016, 20, 798–828; e) D. S. Ryabukhin, A. V.
Vasilyev, Russ. Chem. Rev. 2016, 85, 637–665; f) Priyanka, R. K. Sharma,
D. Katiyar, Synthesis 2016, 48, 2303–2322.
[13] Y. G. Lee, H. Choi, Pat. Rep Korea 2016, KR 1656876.
[14] D. S. Ryabukhin, G. K. Fukin, A. V. Cherkasov, A. V. Vasilyev, Zh. Org.
Khim. 2009, 45, 1260 Russ. J. Org. Chem. (Engl. Transl.) 2009, 45, 1252].
[15] a) P. T. Anastas, J. C. Warner, Green Chemistry: Theory and Practice,
Oxford University Press: Oxford, 1998; b) P. T. Anastas, T. C. Williamson,
Green Chemistry: Frontiers in Benign Synthesis and Practices, Oxford
University Press: Oxford, 1998; c) P. Tundo, P. T. Anastas, Green
Chemistry: Challenging Perspectives, Oxford Science: Oxford, 1999.
[16] a) S. Chassaing, V. Beneteau, P. Pale, Catal. Sci. Technol. 2016, 6, 923–
957; b) S. Chassaing, V. Beneteau, B. Louis, P. Pale, Curr. Org. Chem.
2017, 21, 779–793; c) S. Chassaing, V. Bénéteau, P. Pale, Curr. Opin.
Green Sustain. Chem. 2018, 10, 35–39
[32] π Interaction seems to have a stabilization role in zeolite-promoted
reactions; see: G. Mendonca, A. Bastos, M. Boltz, B. Louis, P. Esteves, P.
Pale, M. De Mattos, Appl. Catal. A 2013, 460–461, 46–51.
Manuscript received: July 30, 2019
[17] a) S. Borghèse, B. Louis, A. Blanc, P. Pale, Catal. Sci. Technol. 2011, 1,
981–986; b) M. Boltz, A. Blanc, G. Laugel, P. Pale, B. Louis, Chin. J. Catal.
2011, 32, 807–811; c) D. Hueber, M. Hoffmann, B. Louis, P. Pale, A. Blanc,
Revised manuscript received: September 13, 2019
Accepted manuscript online: September 18, 2019
Version of record online: ■■■, ■■■■
ChemCatChem 2019, 11, 1–9
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