Artigo Revisado por pares

Layered Double Hydroxide‐Supported L ‐Methionine‐Catalyzed Chemoselective O‐Methylation of Phenols and Esterification of Carboxylic Acids with Dimethyl Carbonate: A “Green” Protocol

2009; Wiley; Volume: 16; Issue: 4 Linguagem: Inglês

10.1002/chem.200902626

ISSN

1521-3765

Autores

Amarajothi Dhakshinamoorthy, Alagarsamy Sharmila, Kasi Pitchumani,

Tópico(s)

Metal-Organic Frameworks: Synthesis and Applications

Resumo

Chemistry – A European JournalVolume 16, Issue 4 p. 1128-1132 Communication Layered Double Hydroxide-Supported L-Methionine-Catalyzed Chemoselective O-Methylation of Phenols and Esterification of Carboxylic Acids with Dimethyl Carbonate: A “Green” Protocol Amarajothi Dhakshinamoorthy Dr., Amarajothi Dhakshinamoorthy Dr. School of Chemistry, Madurai Kamaraj University, Madurai, 625021 Tamil Nadu (India), Fax: (+91) 0452-2459181Search for more papers by this authorAlagarsamy Sharmila, Alagarsamy Sharmila School of Chemistry, Madurai Kamaraj University, Madurai, 625021 Tamil Nadu (India), Fax: (+91) 0452-2459181Search for more papers by this authorKasi Pitchumani Prof. Dr., Kasi Pitchumani Prof. Dr. [email protected] School of Chemistry, Madurai Kamaraj University, Madurai, 625021 Tamil Nadu (India), Fax: (+91) 0452-2459181Search for more papers by this author Amarajothi Dhakshinamoorthy Dr., Amarajothi Dhakshinamoorthy Dr. School of Chemistry, Madurai Kamaraj University, Madurai, 625021 Tamil Nadu (India), Fax: (+91) 0452-2459181Search for more papers by this authorAlagarsamy Sharmila, Alagarsamy Sharmila School of Chemistry, Madurai Kamaraj University, Madurai, 625021 Tamil Nadu (India), Fax: (+91) 0452-2459181Search for more papers by this authorKasi Pitchumani Prof. Dr., Kasi Pitchumani Prof. Dr. [email protected] School of Chemistry, Madurai Kamaraj University, Madurai, 625021 Tamil Nadu (India), Fax: (+91) 0452-2459181Search for more papers by this author First published: 20 January 2010 https://doi.org/10.1002/chem.200902626Citations: 39Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Simple methodology: A layered double hydroxide-supported L-methionine (LDH-Met) catalyst is designed in a simple methodology to explore its synthetic utility in biologically relevant reactions. The organocatalyst is characterized by FT-IR, TGA/DTA, powder XRD, and EDX spectroscopic techniques. This material has been successfully utilized for the preparation of aryl methyl ethers and esters from the corresponding phenols and carboxylic acids, respectively, in moderate to high yields (see scheme). Supporting Information Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description chem_200902626_sm_miscellaneous_information.pdf2.1 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1 Friedel–Crafts and related Reactions, Vol. III (Eds.: ), Wiley-Interscience, New York, 1964. 2J. Cejka, B. Wichterlova, Catal. Rev. Sci. Eng. 2002, 44, 375. 3K. Sreekumar, S. Sugunan, Appl. Catal. A 2002, 230, 245. 4C. Perego, P. Ingallina, Green Chem. 2004, 6, 274. 5A. G. Shaikh, S. Sivaram, Chem. Rev. 1996, 96, 951. 6J. Otera, Angew. Chem. 2001, 113, 2099; Angew. Chem. Int. Ed. 2001, 40, 2044. 7R. C. Larock, Comprehensive Organic Transformations, VCH, Weinheim, 1989, Chapter 9. 8E. Haslam, Tetrahedron 1980, 36, 2409. 9K. Ramalinga, P. Vijayalakshmi, T. N. B. Kaimal, Tetrahedron Lett. 2002, 43, 879. 10G. Pipus, I. Plazl, T. Koloimi, Chem. Eng. J. 2000, 76, 239. 11R. A. Sheldon, R. S. Downing, Appl. Catal. A 1999, 189, 163. 12S. E. Sen, S. M. Smith, K. A. Sulivan, Tetrahedron 1999, 55, 12657. 13A. Pandey, A. P. Singh, Catal. Lett. 1997, 44, 129. 14U. Freese, F. Heinrich, F. Roessner, Catal. Today 1999, 49, 237. 15Y. Ma, Q. L. Wang, H. Yan, X. Ji, Q. Qiu, Appl. Catal. A 1996, 139, 51. 16A. Corma, H. Garcia, S. Iborra, J. Primo, J. Catal. 1989, 120, 78. 17M. Lasperas, P. Graffin, P. Geneste, J. Catal. 1993, 139, 362. 18A. Izci, F. Bodur, React. Funct. Polym. 2007, 67, 1458. 19J. Aracil, M. Martinez, N. Sanchez, A. Corma, Zeolites 1992, 12, 233. 20P. Tundo, Continuous Flow Methods in Organic Synthesis, Horwood, Chichester, 1991. 21M. Aresta, E. Quaranta, Tetrahedron 1991, 47, 9489. 22M. Selva, C. A. Marques, P. Tundo, J. Chem. Soc. Perkin Trans. 1 1994, 1323. 23Z.-H. Fu, Y. Ono, J. Catal. 1994, 145, 166. 24Y. Ono, Appl. Catal. 1997, 155, 136. 25M. Selva, A. Bomben, P. Tundo, J. Chem. Soc. Perkin Trans. 1 1997, 1041. 26P. Tundo, Pure Appl. Chem. 2001, 73, 1117. 27S. Memoli, M. Selva, P. Tundo, Chemosphere 2001, 43, 115. 28M. Selva, P. Tundo, A. Perosa, J. Org. Chem. 2001, 66, 677. 29D. Delledonne, F. Rivetti, U. Romano, Appl. Catal. A 2001, 221, 241. 30P. Tundo, M. Selva, Acc. Chem. Res. 2002, 35, 706. 31P. Tundo, M. Selva, A. Perosa, S. Memoli, J. Org. Chem. 2002, 67, 1071. 32M. Selva, P. Tundo, A. Perosa, J. Org. Chem. 2002, 67, 9238. 33M. Selva, E. Militello, M. Fabris, Green Chem. 2008, 10, 73. 34P. Tundo, S. Memoli, D. Herault, K. Hill, Green Chem. 2004, 6, 609. 35M. Selva, P. Tundo, A. Perosa, F. Dall′Acqua, J. Org. Chem. 2005, 70, 2771. 36M. Selva, P. Tundo, J. Org. Chem. 2005, 70, 2219. 37M. Selva, P. Tundo, A. Perosa, J. Org. Chem. 2003, 68, 7374. 38M. Selva, P. Tundo, T. Foccardi, J. Org. Chem. 2005, 70, 2476. 39M. Selva, P. Tundo, J. Org. Chem. 2006, 71, 1464. 40R. Juarez, A. Padilla, A. Corma, H. Garcia, Catal. Commun. 2009, 10, 472. 41S. Ouk, S. Thiebaud, E. Borredon, P. Legars, Appl. Catal. A 2003, 241, 227. 42S. Ouk, S. Thiebaud, E. Borredon, P. Legars, L. Lecomte, Tetrahedron Lett. 2002, 43, 2661. 43G. Barcelo, D. Grenouillat, J.-P. Senet, G. Sennyey, Tetrahedron 1990, 46, 1839. 44W. C. Shieh, S. Dell, O. Repic, Org. Lett. 2001, 3, 4279. 45A. Perosa, M. Selva, P. Tundo, F. Zordan, Synlett 2000, 272. 46S. R. Kirumakki, N. Nagaraju, K. V. R. Char, S. Narayanan, J. Catal. 2004, 221, 549. 47Z. L. Shen, X. Z. Jiang, W. M. Mo, B. X. Hu, N. Sun, Green Chem. 2005, 7, 97. 48A. Bomben, M. Selva, P. Tundo, Ind. Eng. Chem. Res. 1999, 38, 2075. 49G. Wu, X. Wang, B. Chen, J. Li, N. Zhao, W. Wei, Y. Sun, Appl. Catal. A 2007, 329, 106. 50S. Ouk, S. Thiebaud, E. Borredon, P. LeGars, Green Chem. 2002, 4, 431. 51R. Rhodes, P. Nightingale, WO 86/03485, 1586 Case No 105: 190655 Z, 1986. 52M. Crocker, R. H. M. Herold, J. G. Buglass, P. Companje, J. Catal. 1993, 141, 700. 53C. Li, J. Catal. 2004, 221–228, 419. 54R. Chakrabarty, B. K. Das, J. H. Clark, Green Chem. 2007, 9, 845. 55M. Mora, C. J. -Sanchidrian, J. R. Ruiz, J. Mol. Catal. A 2008, 285, 79. 56B. M. Choudary, M. Roy, S. Roy, M. L. Kantam, J. Mol. Catal. A 2005, 241, 215. 57M. L. Kantam, S. Roy, M. Roy, B. Sreedhar, B. M. Choudary, R. L. De, J. Mol. Catal. A 2007, 273, 26. 58M. L. Kantam, M. Roy, S. Roy, M. S. Subhas, B. Sreedhar, B. M. Choudary, Synlett 2006, 2266. 59K. Okamoto, T. Sasaki, T. Fujita, N. Iyi, J. Mater. Chem. 2006, 16, 1608. 60M. Wei, Z. Shi, D. G. Evans, X. Duan, J. Mater. Chem. 2006, 16, 2102. 61G. L. Cantoni, J. Am. Chem. Soc. 1952, 74, 2942. 62P. Tundo, S. Bressanello, A. Loris, G. Sathicq, Pure Appl. Chem. 2005, 77, 1719. 63M. Selva, P. Tundo, B. Brunelli, A. Perosa, Green Chem. 2007, 9, 463. 64P. Tundo, F. Trotta, G. Moraglio, F. Logorati, Ind. Eng. Chem. Res. 1988, 27, 1565. 65J. N. Greenshields, U.S. Patent 4,770,871, 1988. Citing Literature Volume16, Issue4January 25, 2010Pages 1128-1132 ReferencesRelatedInformation

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