以羧酸为酰化试剂的Friedel-Crafts酰基化反应

  • 白国义 ,
  • 韩捷 ,
  • 闫喜龙
展开
  • 1.河北大学化学与环境科学学院,药物化学与分子诊断教育部重点实验室,河北保定071002; 2.天津大学化工学院,天津,300072

网络出版日期: 2011-11-25

基金资助

国家自然科学基金资助项目,河北省自然科学基金资助项目,河北省教育厅自然科学研究重点计划资助项目

Friedel-Crafts Acylation of Aromatic Compounds with Carboxylic Acids as Acylating Agents

  • BAI Guo-yi ,
  • HAN Jie ,
  • YAN Xi-long
Expand

Online published: 2011-11-25

摘要

分别介绍了以脂肪族和芳香族羧酸为酰化试剂的Friedel-Crafts酰基化反应,重点比较了各种催化剂的优缺点,指出以羧酸为酰化试剂、以环境友好的固体酸为催化剂的Friedel-Crafts酰基化反应是今后芳香酮类化合物合成的发展方向.

本文引用格式

白国义 , 韩捷 , 闫喜龙 . 以羧酸为酰化试剂的Friedel-Crafts酰基化反应[J]. 河北大学学报(自然科学版), 2011 , 31(6) : 658 -667 . DOI: 10.3969/j.issn.1000-1565.2011.06.020

参考文献

[1] 戴立言, 王晓钟, 陈英奇, DAI Li-Yan, WANG Xiao-Zhong, CHEN Ying-Qi. 异黄酮类化合物的合成新方法 [J]. 有机化学 2008.
[2] 白国义, 杨永会, 王磊, BAI Guo-yi, YANG Yong-hui, WANG Lei. 酸改性的Hβ分子筛催化合成乙酰基吡咯 [J]. 河北大学学报(自然科学版) 2011.doi:10.3969/j.issn.1000-1565.2011.02.010
[3] 张祯, 麻远, 赵玉芬, Zhang Zhen, Ma Yuan, Zhao Yufen. 微波辅助的Friedel-Crafts反应 [J]. 化学进展 2008.
[4] 沸石分子筛在Friedel-Crafts酰基化反应中的应用 [J]. 化学进展 2005.doi:10.3321/j.issn:1005-281X.2005.04.015
[5] BEJBLOVá M, PROCHáZKOVá D, ?EJKA J. Acylation reactions over zeolites and mesoporous catalysts [J]. Chemistry Sustainable Chemistry 2009, 2(06).
[6] BAI Guoyi, DOU Haiyang, QIU Mande. Friedel-Crafts hydroxyalkylation of anisole over oxalic acid modified Hβ zeolite [J]. Catalysis Letters 2010, 138(3-4).
[7] Eric Fillion, Dan Fishlock. Total Synthesis of(+-)-Taiwaniaquinol B via a Domino Intramolecular Friedel-Crafts Acylation/Carbonyl alpha-tert-Alkylation Reaction [J]. Journal of the American Chemical Society 2005, 38(38).
[8] BEJBLOVá M, PROCHáZKOVá D, ?EJKA J. Acylation reactions over zeolites and mesoporous catalysts [J]. Chemistry Sustainable Chemistry 2009, 2(06).
[9] Naeimi H, Moradi L. Facile, convenient and regioselective direct ortho-acylation of phenols and naphthols catalyzed by Lewis acids under free solvent and microwave conditions [J]. Journal of molecular catalysis, A. Chemical 2006, 1/2(1/2).
[10] Smyth TP., Corby BW.. Toward a clean alternative to Friedel-Crafts acylation: In situ formation, observation, and reaction of an acyl bis(trifluoroacetyl)phosphate and related structures [J]. The Journal of Organic Chemistry 1998, 24(24).
[11] Luke GP, Seekamp CK, Wang ZQ, Chenard BL. An efficient preparation of beta-aryl-beta-ketophosphonates by the TFAA/H3PO4-mediated acylation of arenes with phosphonoacetic acids [J]. The Journal of Organic Chemistry 2008, 16(16).
[12] Giovanni Sartori, Raimondo Maggi. Use of Solid Catalysts in Friedel-Crafts Acylation Reactions [J]. Chemical Reviews 2006, 3(3).
[13] CHICHE B, FINIELS A, GAUTHIER C. Friedel-Crafts acylation of toluene and p-xylene with carboxylic acids catalyzed by zeolites [J]. Journal of Organic Chemistry 1986, 51(11).
[14] GAUTHIER C, CHICHE B, FINIELS A. Influence of acidity in Friedel-Crafts acylation catalyzed by zeolites [J]. Journal of Molecular Catalysis 1989, 50(02).
[15] WANG Qilong, MA Yudao, JI Xingdong. Regioselective acylation of anisole with carboxylic acids over HZSM-5catalyst [J]. Journal of the Chemical Society, Chemical Communications 1995, 22.
[16] MA Yudao, WANG Qilong, JIANG Wei. Friedal-Crafts acylation of anisole over zeolite catalysts [J]. Applied Catalysis A:General 1997, 165(1-2).
[17] WANG Qilong, MA Yudao, ZUO Bojun. Zeolite-catalyzed Friedel-Crafts reaction of anisole with carboxylic acids [J]. Chinese Journal of Catalysis 1996, 17(05).
[18] WANG Qilong, MA Yudao, JI Xingdong. Zeolite-catalyzed Friedel-Crafts acylation 6f aromatic:Ⅰ.synthsis of 4-acyl anisole with a HY catalyst [J]. Chinese Chemical Letters 1996, 7.
[19] Wagholikar SG, Niphadkar PS, Mayadevi S, Sivasanker S. Acylation of anisole with long-chain carboxylic acids over wide pore zeolites [J]. Applied Catalysis, A. General: An International Journal Devoted to Catalytic Science and Its Applications 2007, 1(1).
[20] A. E. W. Beers, T. A. Nijhuis, F. Kapteijn, J. A. Moulijn. Zeolite coated structures for the acylation of aromatics [J]. Microporous and Mesoporous Materials 2001, 1/3(1/3).
[21] Beers AEW., van Bokhoven JA., de Lathouder KM., Kapteijn F., Moulijn JA.. Optimization of zeolite Beta by steaming and acid leaching for the acylation of anisole with octanoic acid: a structure-activity relation [J]. Journal of Catalysis 2003, 2(2).
[22] Hiroshi Yamashita, Yumi Mitsukura, Hiroko Kobashi. Microwave-assisted acylation of aromatic compounds using carboxylic acids and zeolite catalysts [J]. Journal of molecular catalysis, A. Chemical 2010, 1/2(1/2).
[23] Bond G, Gardner JA, McCabe RW, Shorrock DJ. Friedel-Crafts acylation reactions using heterogeneous catalysts stimulated by conventional and microwave heating [J]. Journal of molecular catalysis, A. Chemical 2007, 1/2(1/2).
[24] OKUHARA T, MIZUNO N, MISONO M. Catalytic chemistry of heteropoly compounds [J]. Advances in Catalysis 1996, 41.
[25] I.V.Kozhevnikov. Friedel-Crafts acylation and related reactions catalysed by heteropoly acids [J]. Applied Catalysis, A. General: An International Journal Devoted to Catalytic Science and Its Applications 2003, 1/2(1/2).
[26] KAUR J, KOZHEVNIKOV I V. Efficient acylation of toluene and anisole with aliphatic carboxylic acids catalyzed by heteropoly salt Cs2.5 H0.5 PW12 O40 [J]. Chemical Communications 2002.
[27] Habib Firouzabadi, Nasser Iranpoor, Farhad Nowrouzi. Solvent-free Friedel-Crafts acylation of aromatic compounds with carboxylic acids in the presence of trifluoroacetic anhydride and aluminum dodecatungstophosphate [J]. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry 2003, 28(28).
[28] Firouzabadi H, Iranpoor N, Nowrouzi F. Aluminum dodecatungstophosphate (AIPW(12)O(40)) as a non-hygroscopic Lewis acid catalyst for the efficient Friedel-Crafts acylation of aromatic compounds under solvent-less conditions [J]. Tetrahedron 2004, 48(48).
[29] Ken-ichi Shimizu, Kenjiro Niimi, Atsushi Satsuma. Polyvalent-metal salts of heteropolyacid as efficient heterogeneous catalysts for Friedel-Crafts acylation of arenes with carboxylic acids [J]. Catalysis Communications 2008, 6(6).
[30] CASTRO C, PRIMO J, CORMA A. Heteropolyacids and large-pore zeolites as catalysts in acylation reactions using α, β-unsaturated organic acids as acylating agents [J]. Journal of Molecular Catalysis A:Chemical 1998, 134(1-3).
[31] CASTRO C, CORMA A, PRIMO J. On the acylation reactions of anisole using α, β-unsaturated organic acids as acylating agents and solid acids as catalysts:a mechanistic overview [J]. Journal of Molecular Catalysis A:Chemical 2002, 177(02).
[32] Masato Kawamura, Dong Mei Cui, Teruyuki Hayashi, Shigeru Shimada. Lewis acid-catalyzed Friedel-Crafts acylation reaction using carboxylic acids as acylating agents [J]. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry 2003, 42(42).
[33] Kawamura M, Cui DM, Shimada S. Friedel-Crafts acylation reaction using carboxylic acids as acylating agents [J]. Tetrahedron 2006, 39(39).
[34] Kobayashi S., Hachiya I., Moriwaki M.. CATALYTIC DIRECT C-ACYLATION OF PHENOL AND NAPHTHOL DERIVATIVES USING CARBOXYLIC ACIDS AS ACYLATING REAGENTS [J]. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry 1996, 24(24).
[35] Hakala U, Wahala K. Microwave-promoted synthesis of polyhydroxydeoxybenzoins in ionic liquids [J]. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry 2006, 47(47).
[36] Yoh-ichi Matsushita, Kazuhiro Sugamoto, Takanao Matsui. The Friedel-Crafts acylation of aromatic compounds with carboxylic acids by the combined use of perfluoroalkanoic anhydride and bismuth or scandium triflate [J]. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry 2004, 24(24).
[37] Plazuk, D, Zakrzewski, J. Friedel-Crafts acylation of ferrocene with alkynoic acids [J]. Journal of Organometallic Chemistry 2009, 12(12).
[38] Damian Plazuk, Janusz Zakrzewski. Acylation of Ferrocene and a 1, 1'-Diphosphaferrocene with Acyl Trifluoroacetates in the Presence of Trifluoromethanesulfonic (Triflic) Acid or Some Metal Triflates [J]. Synthetic Communications 2004, 1(1).
[39] HINOA M, ARATAB K. Acylation of toluene with acetic and benzoic acids catalysed by a solid superacid in a heterogeneous system [J]. Journal of the Chemical Society, Chemical Communications 1985.
[40] Kangani CO, Day BW. Mild, efficient Friedel-Crafts acylations from carboxylic acids using cyanuric chloride and AlCl3 [J]. Organic letters 2008, 13(13).
[41] CORMA A. Acylation of anisole by acyl chlorides or carboxylic acids over acid zeolites [J]. Applied Catalysis A:General 1989, 49(01).
[42] MAY D, WANG Q L, JIANG W. Friedal-Crafts acylation of anisole over zeolite catalysts [J]. Applied Catalysis A:General 1997, 165(1-2).
[43] EARLE M J, HAKALA U, MCAULEY B J. Metal bis{(trifluoromethyl)sulfonyl}amide complexes:highly efficient Friedel-Crafts acylation catalysts [J]. Chemical Communications 2004.
[44] Amin Zarei, Abdol R.Hajipour, Leila Khazdooz. Friedel-Crafts acylation of aromatic compounds with carboxylic acids in the presence of P2O5/SiO2 under heterogeneous conditions [J]. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry 2008, 47(47).
[45] HAJIPOUR A R, ZAREII A, KHAZDOOZ L. Simple and efficient procedure for the Friedel-Crafts acylation of aromatic compounds with carboxylic acids in the presence of P2 O5/Al2 O3 under heterogeneous conditions [J]. Synthetic Communications 2009, 39(15).
[46] Rashid Badri, Laleh Tavakoli. Friedel-Crafts Acylation of Aryl-Substituted Carboxylic Acids Catalyzed by Zeolite [J]. Journal of Inclusion Phenomena and Macrocyclic Chemistry 2003, 1/2(1/2).
[47] Kazuaki Hiroki, Makiko Hatori, Hiroshi Yamashita. Efficient Synthesis of 1-Tetralones from 4-Arylbutyric Acids by Combined Use of Solid Acid Catalysts and Microwave Irradiation [J]. Chemistry Letters 2008, 3(3).
[48] Kamiya Y, Ooka Y, Obara C, Ohnishi R, Fujita T, Kurata Y, Tsuji K, Nakajyo T, Okuhara T. Alkylation-acylation of p-xylene with gamma-butyrolactone or vinylacetic acid catalyzed by heteropolyacid supported on silica [J]. Journal of molecular catalysis, A. Chemical 2007, 1/2(1/2).
[49] YAMATO T, HIDESHIMA C, PRAKASH G K S. Organic reactions catalyzed by solid superacids.5.Perfluorinatedsulfonic acid resin (Nafion-H) catalyzed intramolecular Friedel-Crafts Acylation [J]. Journal of Organic Chemistry 1991, 56(12).
[50] OLAH G A, MATHEW T, FARNIA M. Nafion-H catalysed intramolecular Friedel-Crafts acylation:formation of cyclic ketones and related heterocycles [J]. Synlett:Accounts and Rapid Communications In Synthetic Organic Chemistry 1999, 7.
[51] Dong-Mei Cui, Chen Zhang, Masato Kawamura, Shigeru Shimada. Synthesis of 1-indanones by intramolecular Friedel–Crafts reaction of 3-arylpropionic acids catalyzed by Tb(OTf)_3 [J]. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry 2004, 8(8).
[52] Dong-Mei Cui, Masato Kawamura, Shigeru Shimada, Teruyuki Hayashi, Masato Tanaka. Synthesis of 1-tetralones by intramolecular Friedel-Crafts reaction of 4-arylbutyric acids using Lewis acid catalysts [J]. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry 2003, 21(21).
文章导航

/

〈 〉