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Publicly Available Published by De Gruyter November 18, 2009

Heterogeneous Au and Rh catalysts for cycloisomerization reactions of γ-acetylenic carboxylic acids

  • Florentina Neaţu , Patrick Y. Toullec , Véronique Michelet and Vasile I. Pârvulescu

Abstract

Au- and Rh-based heterogeneized catalytic systems have been prepared and analyzed. Their efficiency has been evaluated for the cycloisomerization of γ-acetylenic carboxylic acids leading to valuable γ-alkylidene γ-butyrolactones. Bulk AuO3 was found to be a valuable and easy-to-handle catalyst for selective transformations, whereas [C6mim][AuCl4] presented a high activity and Au/β-zeolite was recyclable.


Conference

International Symposium on Novel Materials and their Synthesis (NMS-IV) and the 18th International Symposium on Fine Chemistry and Functional Polymers (FCFP-XVIII), Novel Materials and their Synthesis, NMS, Novel Materials and their Synthesis, Zhenjiang, China, 2008-10-15–2008-10-18


References

1a 10.1021/cr0201068, For recent reviews, see: F. Alonso, I. P. Beletskaya, M. Yus. Chem. Rev.104, 3079 (2004).Search in Google Scholar

1b 10.1021/cr020095i, I. Nakamura, Y. Yamamoto. Chem. Rev.104, 2127 (2004).Search in Google Scholar

1c 10.1002/anie.200300616, M. Beller, J. Seayad, A. Tillack, H. Jiao. Angew. Chem., Int. Ed.43, 3368 (2004).Search in Google Scholar

1d 10.1039/b612008c, E. Jimenez-Nunez, A. M. Echavarren. Chem. Commun. 333 (2007). Search in Google Scholar

1e 10.1021/ar980016i, For Ru-catalyzed intermolecular reactions, see: C. Bruneau, P. H. Dixneuf. Acc. Chem. Res.32, 311 (1999).Search in Google Scholar

2a 10.1002/1521-3773(20020201)41:3<414::AID-ANIE414>3.0.CO;2-N, M. E. Eissen, J. O. Metzger, E. Schmidt, U. Schneidewind. Angew. Chem., Int. Ed.41, 414 (2002).Search in Google Scholar

2b P. T. Anastas, J. C. Warner. In Green Chemistry: Theory and Practice, p. 15, Oxford University Press, New York (1998).Search in Google Scholar

3a For a review discussing natural products exhibiting the γ-butyrolactone substructure, see.: S. S. C. Koch, A. R. Chamberlin. In Studies in Natural Products Chemistry, Vol. 16, Atta-ur-Rahman (Ed.), p. 687, Elsevier Science, Amsterdam (1995).Search in Google Scholar

3b 10.1016/j.cbpa.2005.03.005, For reviews discussing the synthetic routes to γ-alkylydene-γ-butyrolactones, see: M. Seitz, O. Reiser. Curr. Opin. Chem. Biol.9, 285 (2005).Search in Google Scholar

3c 10.1016/S0040-4020(97)00199-3, E.-I. Negishi, M. Kotora. Tetrahedron53, 6707 (1997).Search in Google Scholar

3d 10.1039/b007664n, N. B. Carter, A. E. Nadany, J. B. Sweeny. J. Chem. Soc., Perkin Trans 1 2324 (2002).Search in Google Scholar

3e 10.1039/a904715h, I. Collins. J. Chem. Soc., Perkin Trans 1 2845 (2000).Search in Google Scholar

4a For representative examples from Pd chemistry, see: G. Balme, N. Monteiro, D. Bouyssi. Handbook of Organopalladium Chemistry for Organic Synthesis, E.-I. Negishi (Ed.), pp. 2245–2265, John Wiley, New York (2002).Search in Google Scholar

4b T. Hosokawa, S.-I. Murahashi. Handbook of Organopalladium Chemistry for Organic Synthesis, E.-I. Negishi (Ed.), pp. 2169–2192, John Wiley, New York (2002).Search in Google Scholar

4c C. Xu, E.-I. Negishi. Handbook of Organopalladium Chemistry for Organic Synthesis, E.-I. Negishi (Ed.), p. 2289, John Wiley, New York (2002).10.1002/0471212466Search in Google Scholar

5a 10.1016/S0040-4020(01)99293-2, For specific cases of natural product synthesis where cyclizations of alkynoic acids constitute a key step, see: M. Algueró, J. Bosch, J. Castañer, J. Castellá, J. Castells, R. Mestres, J. Pascual, F. Serratosa. Tetrahedron18, 1381 (1962).Search in Google Scholar

5b 10.1021/jo00178a042, T. T. Jong, P. G. Williard, J. P. Porwoll. J. Org. Chem.49, 735 (1984).Search in Google Scholar

5c 10.1055/s-2006-926257, H. Imagawa, Y. Fujikawa, A. Tsuchihiro, A. Kinoshita, T. Yoshinaga, H. Takao, N. Nishizawa. Synlett 639 (2006).Search in Google Scholar

6a 10.1021/np050510c, A. D. Wright, R. de Nys, C. K. Angerhofer, J. M. Pezzuto, M. Gurrath. J. Nat. Prod.69, 1180 (2006).Search in Google Scholar

6b 10.1021/np060107l, C.-H. Chen, W.-L. Lo, Y.-C. Liu, C.-Y. Chen. J. Nat. Prod.69, 927 (2006).Search in Google Scholar

7a 10.1039/jr9580003962, Silver catalysis.: J. Castaner, J. Pascual. J. Chem. Soc. 3962 (1958).Search in Google Scholar

7b 10.1016/S0040-4039(00)96884-9, P. Pale, J. Chuche. Tetrahedron Lett.28, 6447 (1987).Search in Google Scholar

7c 10.1039/a903587g, V. Dalla, P. Pale. New J. Chem.23, 803 (1999).Search in Google Scholar

7d 10.1016/S0040-4039(00)73226-6, V. Dalla, P. Pale. Tetrahedron Lett.35, 3525 (1994).Search in Google Scholar

7e 10.1039/b702704d, C. H. Oh, H. J. Yi, J. H. Lee. New J. Chem.31, 835 (2007).Search in Google Scholar

8a 10.1039/c39780000649, Mercury catalysis: M. Yamamoto. J. Chem. Soc., Chem. Commun. 649 (1978).Search in Google Scholar

8b 10.1039/p19810000582, M. Yamamoto. J. Chem. Soc., Perkin Trans. 1 582 (1981).Search in Google Scholar

8c 10.1021/jo00398a007, R. A. Amos, J. A. Katzenellenbogen. J. Org. Chem.43, 560 (1978).Search in Google Scholar

8d R. A. Amos, J. A. Katzenellenbogen. J. Am. Chem. Soc.103, 5459 (1981).Search in Google Scholar

8e 10.1021/ja00404a023, S. W. Rollinson, R. A. Amos, J. A. Katzenellenbogen. J. Am. Chem. Soc.103, 4114 (1981).Search in Google Scholar

8f 10.1021/jo00213a026, M. J. Sofia, J. A. Katzenellenbogen. J. Org. Chem.50, 2331 (1984).Search in Google Scholar

8g 10.1021/ja00278a038, R. W. Spencer, T. F. Tam, E. Thomas, V. J. Robinson, A. Krantz. J. Am. Chem. Soc.108, 5589 (1986).Search in Google Scholar

8h 10.1016/S0040-4039(01)91002-0, A. Jellal, J. Grimaldi, M. Santelli. Tetrahedron Lett.25, 3179 (1984).Search in Google Scholar

9a 10.1016/S0040-4039(01)81594-X, Palladium catalysis: C. Lambert, K. Utimoto, H. Nozaki. Tetrahedron Lett.25, 5323 (1984).Search in Google Scholar

9b 10.1021/ja00270a043, N. Yanagihara, C. Lambert, K. Iritari, K. Utimoto, H. Nozaki. J. Am. Chem. Soc.108, 2753 (1986).Search in Google Scholar

9c 10.1021/jo00029a035, A. Arcadi, A. Burini, S. Cacchi, M. Delmastro, F. Marinelli, B. R. Pietroni. J. Org. Chem.57, 976 (1992).Search in Google Scholar

9d 10.1016/0040-4039(96)00063-9, M. Cavicchioli, D. Bouyssi, J. Goré, G. Balme. Tetrahedron Lett.37, 1429 (1996).Search in Google Scholar

9e 10.1021/jo9522466, X. Wang, X. Lu. J. Org. Chem.61, 2254 (1996).Search in Google Scholar

9f 10.1002/adsc.200600507, Z. Huo, N. T. Patil, T. Jin, N. K. Pahadi, Y. Yamamoto. Adv. Synth. Catal.349, 680 (2007).Search in Google Scholar

9g 10.1016/S0040-4020(00)00125-3, F. Bellina, D. Ciucci, P. Vergamini, R. Rossi. Tetrahedron56, 2533 (2000).Search in Google Scholar

9h 10.1002/ejoc.200500142, Z. Ahmed, U. Albrecht, P. Langer. Eur. J. Org. Chem. 3469 (2005).Search in Google Scholar

9i 10.1021/jo050440e, V. Subramanian, V. R. Batchu, D. Barange, M. Pal. J. Org. Chem.70, 4778 (2005).Search in Google Scholar PubMed

9j A. Duchêne, J. Thibonnet, J.-L. Parrain, E. Anselmi, M. Abarbri. Synthesis 597 (2007).10.1055/s-2007-966043Search in Google Scholar

10 10.1039/b106647c, Ruthenium catalysis: M. Jimenez-Tenotio, M. C. Puerta, P. Valerga, F. J. Moreno-Dorado, F. M. Guerra, G. M. Massanet. Chem. Commun. 2324 (2001).Search in Google Scholar PubMed

11a 10.1039/c39870001885, Rhodium catalysis: T. B. Marder, D. M. T. Chan, W. C. Fultz, J. C. Calabrese, D. J. Milstein. J. Chem. Soc., Chem Commun. 1885 (1987).Search in Google Scholar

11b 10.1021/ja00255a025, D. M. T. Chan, T. B. Marder, D. Milstein, N. J. Taylor. J. Am. Chem. Soc.109, 6385 (1987).Search in Google Scholar

11c 10.1016/S0022-328X(00)00233-3, S. Elgafi, L. D. Field, B. A. Messerle. J. Organomet. Chem.607, 97 (2000).Search in Google Scholar

12a Cluster catalysis: T. Wakabayashi, Y. Ishii, K. Ishikawa, M. Hidai. Angew. Chem., Int. Ed.35, 3123 (1996) and refs. cited therein.10.1002/anie.199621231Search in Google Scholar

12b 10.1021/om034097k, I. Takei, Y. Wakebe, K. Suzuki, Y. Enta, T. Suzuki, Y. Mizobe, M. Hidai. Organometallics22, 4639 (2003).Search in Google Scholar

13a 10.1246/cl.1987.405, M. Haruta, T. Kobayashi, H. Sano, N. Yamada. Chem. Lett.16, 405 (1987).Search in Google Scholar

13b 10.1016/S0167-2991(09)61278-7, M. Haruta, H. Kageyama, N. Kamijo, T. Kobayashi, F. Delannay. Stud. Surf. Sci. Catal.44, 33 (1989).Search in Google Scholar

13c 10.1016/0021-9517(89)90034-1, M. Haruta, N. Yamada, T. Kobayashi, S. Iijima. J. Catal.115, 301 (1989).Search in Google Scholar

13d 10.1002/anie.200502382, B. Chowdhury, J. J. Bravo-Suarez, M. Date, S. Tsubota, M. Haruta. Angew. Chem., Int. Ed.45, 412 (2006).Search in Google Scholar PubMed

14a 10.1002/anie.200604335, For representative examples and seminal references, see: A. Fürstner, P. W. Davies. Angew Chem., Int. Ed.46, 3410 (2007).Search in Google Scholar PubMed

14b 10.1038/nature05592, D. J. Gorin, D. Toste. Nature446, 395 (2007).Search in Google Scholar PubMed

14c 10.1002/anie.200602454, A. S. K. Hashmi, G. J. Hutchings. Angew. Chem., Int. Ed.45, 7896 (2006).Search in Google Scholar PubMed

14d 10.1039/b612008c, E. Jimenez-Nunez, A. M. Echavarren. Chem. Commun. 333 (2007).Search in Google Scholar PubMed

14e 10.1002/anie.200502999, S. Ma, S. Yu, Z. Gu. Angew. Chem., Int. Ed.45, 200 (2006).Search in Google Scholar PubMed

14f A. S. K. Hashmi. Angew. Chem., Int. Ed.44, 6090 (2005).Search in Google Scholar

14g 10.1039/b416516k, A. Höffmann-Röder, N. Krause. Org. Biomol. Chem.3, 387 (2005).Search in Google Scholar PubMed

14h A. S. K. Hashmi. Gold Bull.37, 51 (2004).10.1007/BF03215517Search in Google Scholar

14i 10.1002/anie.200300624, P. Pyykkö. Angew. Chem., Int. Ed.43, 4412 (2004).Search in Google Scholar PubMed

14j 10.1021/cr000436x, A. S. K. Hashmi. Chem. Rev.107, 3180 (2007).Search in Google Scholar PubMed

14k C. Frank Shaw III. Chem. Rev.99, 2589 (1999).10.1021/cr980431oSearch in Google Scholar PubMed

14l 10.1002/anie.200701589, V. Michelet, P. Y. Toullec, J.-P. Genet. Angew. Chem., Int. Ed.47, 4268 (2008).Search in Google Scholar PubMed

14m 10.1021/cr068435d, A. Arcadi. Chem. Rev.108, 3266 (2008).Search in Google Scholar PubMed

14n 10.1021/cr050041j, N. T. Patil, Y. Yamamoto. Chem. Rev.108, 3395 (2008).Search in Google Scholar PubMed

14o 10.1021/cr068434l, Z. Li, C. Brouwer, C. He. Chem. Rev.108, 3239 (2008).Search in Google Scholar PubMed

14p 10.1016/j.tet.2008.01.081, H. C. Shen. Tetrahedron64, 3885 (2008).Search in Google Scholar

14q 10.1016/j.tet.2008.03.083, R. Skouta, C.-J. Li. Tetrahedron64, 4917 (2008).Search in Google Scholar

14r 10.1039/b615629k, A. S. K. Hashmi, M. Rudolph. Chem. Soc. Rev.37, 1766 (2008).Search in Google Scholar PubMed

14s 10.1016/j.tet.2008.04.018, J. Muzart. Tetrahedron64, 5815 (2008).Search in Google Scholar

14t 10.1021/cr000436x, A. S. K. Hashmi. Chem. Rev.107, 3180 (2007).Search in Google Scholar PubMed

15a 10.1021/ja0530671, S. Antoniotti, E. Genin, V. Michelet, J.-P. Genêt. J. Am. Chem. Soc.127, 9976 (2005).Search in Google Scholar PubMed

15b 10.1002/anie.200501150, E. Genin, S. Antoniotti, V. Michelet, J.-P. Genêt. Angew. Chem., Int. Ed.44, 4949 (2005).Search in Google Scholar PubMed

16a 10.1021/ja056857j, E. Genin, P. Y. Toullec, S. Antoniotti, C. Brancour, J.-P. Genêt, V. Michelet. J. Am. Chem. Soc.128, 3112 (2006).Search in Google Scholar PubMed

16b E. Genin, P. Y. Toullec, S. Antoniotti, C. Brancour, J.-P. Genêt, V. Michelet. ARKIVOCv, 67 (2007).10.3998/ark.5550190.0008.507Search in Google Scholar

17a 10.1016/j.tetlet.2006.06.129, H. Harkat, J.-M. Weibel, P. Pale. Tetrahedron Lett.47, 6273 (2006).Search in Google Scholar

17b 10.1016/j.tet.2007.07.066, For a recent Au-catalyzed cyclization of γ- and δ-acetylenic acids, see: E. Marchal, P. Uriac, B. Legoin, L. Toupet, P. van de Weghe. Tetrahedron63, 9979 (2007).Search in Google Scholar

18a 10.1021/jo00011a058, For references dealing with the gold-catalyzed hydration of alkynes, see: Y. Fukuda, K. Utimoto. J. Org. Chem.56, 3729 (1991).Search in Google Scholar

18b 10.1002/(SICI)1521-3773(19980605)37:10<1415::AID-ANIE1415>3.0.CO;2-N, J. H. Teles, S. Brode, M. Chabanas. Angew. Chem., Int. Ed.37, 1415 (1998).Search in Google Scholar

18c 10.1002/1521-3773(20021202)41:23<4563::AID-ANIE4563>3.0.CO;2-U, E. Mizushima, K. Sato, T. M. Hayashi. Angew. Chem., Int. Ed.41, 4563 (2002).Search in Google Scholar

18d 10.1002/zaac.200300247, S. K. Schneider, W. A. Herrmann, E. Herdtweck. Z. Anorg. Allg. Chem.629, 2363 (2003).Search in Google Scholar

19 P. Y. Toullec, E. Genin, S. Antoniotti, J.-P. Genêt, V. Michelet. Synlett 707 (2008).10.1055/s-2008-1032108Search in Google Scholar

20a 10.1021/ol062190+, M. Uchiyama, H. Ozawa, K. Takuma, Y. Matsumoto, M. Yonehara, K. Hiroya, T. Sakamoto. Org. Lett.8, 5517 (2006).Search in Google Scholar

20b 10.1016/j.tetlet.2006.12.015, C. Kanazawa, M. Terada. Tetrahedron Lett.48, 933 (2007).Search in Google Scholar

21 10.1016/S0167-2991(08)80069-9, F. Neaţu, K. Triantafyllidis, J.-P. Genêt, V. Michelet, V. I. Pârvulescu. Stud. Surf. Sci. Catal. (A. Gedeon, P. Massiani, F. Babonneau, Eds.) 174B, 1057 (2008).Search in Google Scholar

22a 10.1002/chem.200701263, A. Abad, A. Corma, H. Garcia. Chem.—Eur. J.14, 212 (2008) and refs. therein.Search in Google Scholar PubMed

22b 10.1039/b707314n, A. Corma, H. Garcia. Chem. Soc. Rev.37, 2096 (2008).Search in Google Scholar PubMed

23 R. J. David. Science301, 926 (2003) and refs. therein.Search in Google Scholar

24 10.1016/j.jcat.2007.04.016, Z.-R. Tang, J. K. Edwards, J. K. Bartley, S. H. Taylor, A. F. Carley, A. A. Herzing, C. J. Kiely, G. J. Hutchings. J. Catal.249, 208 (2007) and refs. therein.Search in Google Scholar

25 10.1039/b812580e, F. Neaţu, V. I. Pârvulescu, V. Michelet, J.-P. Gênet, A. Goguet, C. Hardacre. New J. Chem.1, 102 (2009).Search in Google Scholar

26a 10.1126/science.1128383, A. Corma, P. Serna. Science313, 332 (2006) and refs. herein.Search in Google Scholar PubMed

26b 10.1002/anie.200500659, J. Guzman, S. Carrettin, J. C. Fierro-Gonzalez, Y. Hao, B. C. Gates, A. Corma. Angew. Chem., Int. Ed.44, 4778 (2005).Search in Google Scholar PubMed

26c 10.1002/anie.200353570, S. Carrettin, P. Concepción, A. Corma, J. M. López-Nieto, V. F. Puntes. Angew. Chem., Int. Ed.43, 2538 (2004).Search in Google Scholar PubMed

27a 10.1002/anie.200462560, S. Carrettin, J. Guzman, A. Corma. Angew. Chem., Int. Ed.44, 2242 (2005).Search in Google Scholar PubMed

27b S. Carrettin, A. Corma, M. Iglesias, F. Sanchez. Appl. Catal., A291, 247 (2005).10.1016/j.apcata.2005.01.047Search in Google Scholar

27c 10.1002/anie.200604746, C. Gonzales-Arellano, A. Abad, A. Corma, H. Garcia, M. Iglesias, F. Sanchez. Angew. Chem., Int. Ed.46, 1536 (2007).Search in Google Scholar PubMed

27d 10.1002/adsc.200606163, A. Corma, E. Gutierrez-Puebla, M. Iglesias, A. Monge, S. Perez-Ferreras, F. Sanchez. Adv. Synth. Catal.348, 1899 (2006).Search in Google Scholar

27e 10.1002/adsc.200606099, S. Carrettin, M. C. Blanco, A. Corma, A. S. K. Hashmi. Adv. Synth. Catal.348, 1283 (2006).Search in Google Scholar

28 10.1002/chem.200801327, F. Neaţu, Z. Li, R. Richards, P. Y. Toullec, J.-P. Genêt, K. Dumbuya, J. M. Gottfried, H.-P. Steinrück, V. I. Pârvulescu, V. Michelet. Chem.—Eur. J.14, 9412 (2008).Search in Google Scholar PubMed

Published Online: 2009-11-18
Published in Print: 2009-11-18

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