%0 Journal Article %1 ISI:000288128600019 %A Mohammadpoor-Baltork, Iraj %A Moghadam, Majid %A Tangestaninejad, Shahram %A Mirkhani, Valiollah %A Mohammadiannejad-Abbasabadi, Kazem %A Khavasi, Hamid R. %C COMMERCE PLACE, 350 MAIN ST, MALDEN 02148, MA USA %D 2011 %I WILEY-BLACKWELL %J EUROPEAN JOURNAL OF ORGANIC CHEMISTRY %K Arenes; Carbocycles; Green Triarylmethanes} chemistry; coupling; {C-C %N 7 %P 1357-1366 %R 10.1002/ejoc.201001267 %T H3PW12O40-Catalysed Alkylation of Arenes and Diveratrylmethanes: Convenient Routes to Triarylmethanes and to Symmetrical and Unsymmetrical 9,10-Diaryl-2,3,6,7-tetramethoxyanthracenes %X An efficient method for the synthesis of triarylmethanes and difurylarylmethanes through solventless reactions between aldehydes and arenes in the presence of H3PW12O40 as a reusable catalyst under thermal and microwave irradiation conditions has been developed. H3PW12O40-catalysed one-pot consecutive Friedel-Crafts reactions between veratrole and aldehydes were also applied as a convenient protocol for the preparation of symmetrical 9,10-diaryl-2,3,6,7-tetramethoxyanthracenes. The conversion of aldehydes into their corresponding acylals in the presence of H3PW12O40 and the one-pot reactions of diveratrylmethanes with these acylals were also used for the synthesis of symmetrical and unsymmetrical 9,10-diaryl-2,3,6,7-tetramethoxyanthracenes.

@article{ISI:000288128600019, abstract = {{An efficient method for the synthesis of triarylmethanes and difurylarylmethanes through solventless reactions between aldehydes and arenes in the presence of H3PW12O40 as a reusable catalyst under thermal and microwave irradiation conditions has been developed. H3PW12O40-catalysed one-pot consecutive Friedel-Crafts reactions between veratrole and aldehydes were also applied as a convenient protocol for the preparation of symmetrical 9,10-diaryl-2,3,6,7-tetramethoxyanthracenes. The conversion of aldehydes into their corresponding acylals in the presence of H3PW12O40 and the one-pot reactions of diveratrylmethanes with these acylals were also used for the synthesis of symmetrical and unsymmetrical 9,10-diaryl-2,3,6,7-tetramethoxyanthracenes.}}, added-at = {2017-05-10T15:29:29.000+0200}, address = {{COMMERCE PLACE, 350 MAIN ST, MALDEN 02148, MA USA}}, affiliation = {{Mohammadpoor-Baltork, I (Reprint Author), Univ Isfahan, Catalysis Div, Dept Chem, Esfahan 8174673441, Iran. Mohammadpoor-Baltork, Iraj; Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiollah; Mohammadiannejad-Abbasabadi, Kazem, Univ Isfahan, Catalysis Div, Dept Chem, Esfahan 8174673441, Iran. Khavasi, Hamid R., Shahid Beheshti Univ, Dept Chem, Tehran 1983963113, Iran.}}, author = {Mohammadpoor-Baltork, Iraj and Moghadam, Majid and Tangestaninejad, Shahram and Mirkhani, Valiollah and Mohammadiannejad-Abbasabadi, Kazem and Khavasi, Hamid R.}, author-email = {{imbaltork@sci.ui.ac.ir}}, biburl = {https://www.bibsonomy.org/bibtex/234ff72421c103004da63831b6414ac4a/hkhavasi}, cited-references = {{Ahmad R, 2009, TETRAHEDRON LETT, V50, P1490, DOI 10.1016/j.tetlet.2009.01.079. AHMED M, 1973, J CHEM SOC PERK T 1, P1099, DOI 10.1039/p19730001099. Ando S, 2005, CHEM MATER, V17, P1261, DOI 10.1021/cm0478632. Anthony JE, 2006, CHEM REV, V106, P5028, DOI 10.1021/cr050966z. Arganat I., 1974, SYNTHESIS-STUTTGART, P865. Barclay L. R. C., 1964, FRIEDEL CRAFTS RELAT, VII. Beletskaya IP, 2002, TETRAHEDRON LETT, V43, P1193, DOI 10.1016/S0040-4039(01)02356-5. BRADSHER CK, 1946, CHEM REV, V38, P447, DOI 10.1021/cr60121a003. Cho DM, 2005, ORG LETT, V7, P1067, DOI 10.1021/ol050019c. CHUNSOG X, 2007, ORG LETT, V9, P781. Danel K, 2002, CHEM MATER, V14, P3860, DOI 10.1021/cm020250. de la Hoz A, 2005, CHEM SOC REV, V34, P164, DOI 10.1039/b411438h. Dimitrakopoulos CD, 2002, ADV MATER, V14, P99, DOI 10.1002/1521-4095(20020116)14:2<99::AID-ADMA99>3.0.CO;2-9. Dubury D.F., 1993, CHEM REV, V93, P381. Esquivias J, 2006, ANGEW CHEM INT EDIT, V45, P629, DOI 10.1002/anie.200503305. Fieser L. F., 1942, ORG REACTIONS, V1, P129. Genovese S., 2009, EUR J ORG CHEM, V8, P1132, DOI DOI 10.1002/EJ0C.200801115. Gondek E, 2008, MATER CHEM PHYS, V112, P301, DOI 10.1016/j.matchemphys.2008.05.054. Goossens R, 2002, TETRAHEDRON LETT, V43, P6605, DOI 10.1016/S0040-4039(02)01462-4. Gunnlaugsson T, 2004, TETRAHEDRON, V60, P11239, DOI 10.1016/j.tet.2004.08.047. HALL N, 1994, SCIENCE, V266, P32, DOI 10.1126/science.266.5182.32. Hammett LP, 1937, J AM CHEM SOC, V59, P96, DOI 10.1021/ja01280a022. Hashmi ASK, 2007, CHEM REV, V107, P3180, DOI 10.1021/cr000436x. Hashmi ASK, 2007, CATAL TODAY, V122, P211, DOI 10.1016/j.cattod.2006.10.006. Hashmi ASK, 2006, ANGEW CHEM INT EDIT, V45, P7896, DOI 10.1002/anie.200602454. Hashmi ASK, 2010, ANGEW CHEM INT EDIT, V49, P5232, DOI 10.1002/anie.200907078. Hashmi ASK, 2006, ADV SYNTH CATAL, V348, P705, DOI 10.1002/adsc.200505464. Hayes BL, 2004, ALDRICHIM ACTA, V37, P66. He QL, 2009, SYNLETT, P1111, DOI 10.1055/s-0028-1088109. Hua DH, 2002, J ORG CHEM, V67, P2907, DOI 10.1021/jo010958s. Itp K., 2003, ANGEW CHEM INT EDIT, V42, P1159. Kappe O.C., 2004, ANGEW CHEM INT EDIT, V43, P6250. KAPPE OC, 2006, NAT REV, V5, P51. KAPPE OC, 2008, CHEM SOC REV, V37. Katritzky AR, 1997, J ORG CHEM, V62, P4137, DOI 10.1021/jo9624197. Katsoulis DE, 1998, CHEM REV, V98, P359, DOI 10.1021/cr960398a. Kodomari M, 2008, TETRAHEDRON LETT, V49, P2537, DOI 10.1016/j.tetlet.2008.02.117. Kotha S, 2002, SYNLETT, P451. Kozhevnikov IV, 1998, CHEM REV, V98, P171, DOI 10.1021/cr960400y. Landis CA, 2005, JPN J APPL PHYS 1, V44, P3921, DOI 10.1143/JJAP.44.3921. Li G, 2007, J ORG CHEM, V72, P9830, DOI 10.1021/jo7017334. Li ZX, 2008, TETRAHEDRON, V64, P1924, DOI 10.1016/j.tet.2007.11.080. Lin SH, 2007, J ORG CHEM, V72, P9757, DOI 10.1021/jo071232k. Meng H, 2005, J AM CHEM SOC, V127, P2406, DOI 10.1021/ja043189d. Misono M, 2001, CHEM COMMUN, P1141, DOI 10.1039/b102573m. Miyai T, 1999, TETRAHEDRON, V55, P1017, DOI 10.1016/S0040-4020(98)01130-2. Mohammadpoor-Baltork I, 2008, POLYHEDRON, V27, P2612, DOI 10.1016/j.poly.2008.05.002. Mohammadpoor-Baltork I, 2008, CATAL COMMUN, V9, P1153, DOI 10.1016/j.catcom.2007.10.026. Mohammadpoor-Baltork I, 2008, POLYHEDRON, V27, P750, DOI 10.1016/j.poly.2007.11.018. Mondal R, 2006, J ORG CHEM, V71, P4085, DOI 10.1021/jo0601314. Morrison DJ, 2005, J ORG CHEM, V70, P5309, DOI 10.1021/jo0506231. Nair V, 2005, ORG LETT, V7, P5857, DOI 10.1021/o1052423h. Nair V, 2006, TETRAHEDRON, V62, P6731, DOI 10.1016/j.tet.2006.04.081. Niwa T, 2007, ORG LETT, V9, P2373, DOI 10.1021/ol0708119. Ostaszewski R, 1998, TETRAHEDRON, V54, P6897, DOI 10.1016/S0040-4020(98)00370-6. Parai MK, 2008, BIOORG MED CHEM LETT, V18, P289, DOI 10.1016/j.bmcl.2007.10.083. Park CS, 2009, TETRAHEDRON LETT, V50, P671, DOI 10.1016/j.tetlet.2008.11.090. Perreux L, 2001, TETRAHEDRON, V57, P9199, DOI 10.1016/S0040-4020(01)00905-X. Poder S., 2007, J ORG CHEM, V72, P3100, DOI DOI 10.1021/J0062633N. POPE M, 1963, J CHEM PHYS, V38, P2042, DOI 10.1063/1.1733929. SAITO S, 1995, J AM CHEM SOC, V117, P11081, DOI 10.1021/ja00150a007. Shchepinov MS, 2003, CHEM SOC REV, V32, P170, DOI 10.1039/b0089001. SHUHONG L, 2008, TETRAHEDRON LETT, V49, P1690. Smet M, 1999, TETRAHEDRON, V55, P7859, DOI 10.1016/S0040-4020(99)00406-8. Sun FL, 2009, CHEM-EUR J, V15, P8709, DOI 10.1002/chem.200901369. Swartz CR, 2005, ORG LETT, V7, P3163, DOI 10.1021/ol050872b. Takahashi T, 2002, J AM CHEM SOC, V124, P576, DOI 10.1021/ja016848k. Tanaka K, 2000, CHEM REV, V100, P1025, DOI 10.1021/cr940089p. TIETZE LF, 1993, ANGEW CHEM INT EDIT, V32, P131, DOI 10.1002/anie.199301313. Tietze LF, 1996, CHEM REV, V96, P115, DOI 10.1021/cr950027e. Varazo K, 2008, TETRAHEDRON LETT, V49, P5293, DOI 10.1016/j.tetlet.2008.06.092. VINCETT PS, 1982, THIN SOLID FILMS, V94, P171, DOI 10.1016/0040-6090(82)90509-0. Wang GW, 2008, EUR J ORG CHEM, P4367, DOI 10.1002/ejoe.200800413. Yamato T, 1997, J CHEM SOC PERK T 1, P1193, DOI 10.1039/a606205i. Yu JY, 2008, ORG LETT, V10, P973, DOI 10.1021/ol800078j.}}, doc-delivery-number = {{731SC}}, doi = {{10.1002/ejoc.201001267}}, funding-acknowledgement = {{Centre of Excellence of Chemistry; Research Council of the University of Isfahan}}, funding-text = {{The authors thank the Centre of Excellence of Chemistry and Research Council of the University of Isfahan for financial support for this work.}}, interhash = {266a35c05ede10e836c1f104a2e2618a}, intrahash = {34ff72421c103004da63831b6414ac4a}, issn = {{1434-193X}}, journal = {{EUROPEAN JOURNAL OF ORGANIC CHEMISTRY}}, journal-iso = {{Eur. J. Org. Chem.}}, keywords = {Arenes; Carbocycles; Green Triarylmethanes} chemistry; coupling; {C-C}, keywords-plus = {{HOMOGENEOUS GOLD CATALYSIS; FRIEDEL-CRAFTS REACTION; ELECTRON-RICH ARENES; SUBSTITUTED ANTHRACENES; ORGANIC-SYNTHESIS; 12-TUNGSTOPHOSPHORIC ACID; PHOTOPHYSICAL PROPERTIES; SELECTIVE PREPARATION; AROMATIC-ALDEHYDES; ARYLBORONIC ACIDS}}, language = {{English}}, month = {{MAR}}, number = {{7}}, number-of-cited-references = {{75}}, pages = {{1357-1366}}, publisher = {{WILEY-BLACKWELL}}, research-areas = {{Chemistry}}, times-cited = {{12}}, timestamp = {2017-05-10T15:29:29.000+0200}, title = {{H3PW12O40-Catalysed Alkylation of Arenes and Diveratrylmethanes: Convenient Routes to Triarylmethanes and to Symmetrical and Unsymmetrical 9,10-Diaryl-2,3,6,7-tetramethoxyanthracenes}}, type = {{Article}}, unique-id = {{ISI:000288128600019}}, usage-count-last-180-days = {{0}}, usage-count-since-2013 = {{12}}, web-of-science-categories = {{Chemistry, Organic}}, year = {{2011}} }