Zinc Mediated Friedel-Crafts Acylation in Solvent-Free Conditions under Microwave Irradiation

Satya Paul; Puja Nanda; Rajive Gupta; André Loupy

doi:10.1055/s-2003-42485

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2003(18): 2877-2881
DOI: 10.1055/s-2003-42485

PAPER

Zinc Mediated Friedel-Crafts Acylation in Solvent-Free Conditions under Microwave Irradiation

Satya Paul^a, Puja Nanda^a, Rajive Gupta*^a, André Loupy^b
^a Department of Chemistry, University of Jammu, Jammu-180 006, India
Fax: 91(191)505086; e-Mail: rajgupta@sancharnet.in;
^b Laboratoire des Réactions Sélectives sur Supports, CNRS UMR 8615, Université Paris-Sud, 91405, Orsay, France
Fax: 33(1)69154679; e-Mail: aloupy@icmo.u-psud.fr;

Further Information

Publication History

Received 17 September 2003
Publication Date:
17 November 2003 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Zn powder is found to catalyze the Friedel-Crafts acylation of aromatic compounds with acyl halides efficiently under microwave irradiation in solvent-free conditions. Activated substrates undergo acylation predominantly at the para-position. The Zn powder can be re-used up to six times after simple washing with diethyl ether and dilute HCl.

Key words

Friedel-Crafts acylation - zinc powder - aromatic compounds - solvent-free conditions - microwave activation

References

1 Kawada A. Mitamura S. Kobayashi S. J. Chem. Soc., Chem. Commun. 1996, 183

Google Scholar
2 Izumi J. Mukaiyama T. Chem. Lett. 1996, 739

Google Scholar
3 Kusama H. Narasaka K. Bull. Chem. Soc. Jpn. 1995, 68: 2379

Crossref Google Scholar
4 Bartoli G. Bosco M. Marcantoni E. Massaceri M. Rinaldi S. Sambri L. Tetrahedron Lett. 2002, 43: 6331

Crossref Google Scholar
5 Pai SG. Bajpai AR. Deshpande AB. Samant SD. Synth. Commun. 1997, 27: 2267

Crossref Google Scholar
6 Farkes J. Be Kassy S. Agai B. Hegeders M. Figueras F. Synth. Commun. 2000, 30: 2479

Crossref Google Scholar
7 Bastock TW. Clark JH. Landon P. Martin K. J. Chem. Res., Synop. 1994, 104

Google Scholar
8 Chiche B. Finiels A. Gauthier G. Geneste P. J. Org. Chem. 1986, 51: 2128

Crossref Google Scholar
9 Wang QL. Ma Y. Ji X. Yan H. Qiu Q. J. Chem. Soc., Chem. Commun. 1995, 2307

Crossref Google Scholar
10 Ranu BC. Ghosh K. Jana U. J. Org. Chem. 1996, 61: 9546

Crossref Google Scholar
11 Hydtoft L. Madsen R. J. Am. Chem. Soc. 2000, 122: 8444

Crossref Google Scholar
12 Bertozzi F. Olsson R. Frejd T. Org. Lett. 2000, 2: 1283

Crossref Google Scholar
13 Ogawa Y. Saiga A. Mori M. Shibata T. Takegi K. J. Org. Chem. 2000, 65: 1031

Crossref Google Scholar
14 Chavan SP. Shivasankar K. Sivappa R. Kale R. Tetrahedron Lett. 2002, 43: 8583

Crossref Google Scholar
15 Yadav JS. Reddy BVS. Kondaji G. Rao RS. Kumar SP. Tetrahedron Lett. 2002, 43: 8133

Crossref Google Scholar
16a Varma RS. Green Chem. 1999, 1: 43

Crossref Google Scholar
16b Loupy A. Petit A. Hamelin J. Texier-Boullet F. Jacquault P. Mathé D. Synthesis 1998, 1213

Crossref Google Scholar
16c de la Hoz A. Diaz-Ortis A. Moreno A. Langa F. Eur. J. Org. Chem. 2000, 3659

Crossref Google Scholar
16d Lidström P. Tierney J. Wathey B. Westman J. Tetrahedron 2001, 57: 9225

Crossref Google Scholar
16e Microwaves in Organic Synthesis Loupy A. Wiley-VCH; Weinheim: 2002.

Crossref Google Scholar
17a Laporte C. Marquié J. Laporterie A. Desmurs JR. Dubac J. C. R. Acad. Sci. 1999, 455

Crossref Google Scholar
17b Marquié J. Laporte C. Laporterie A. Dubac J. Desmurs JR. Roques N. Ind. Eng. Chem. Res. 2000, 39: 1124

Crossref Google Scholar
17c Marquié J. Laporterie A. Dubac J. Roques N. Desmurs JR. J. Org. Chem. 2001, 66: 421

Crossref Google Scholar
18a Varma RS. In Green Chemistry: Challenging Perspectives Tundo P. Anastas PT. Oxford University Press; Oxford: 2000. p.221-244

Crossref Google Scholar
18b Varma RS. Tetrahedron 2002, 58: 1235

Crossref Google Scholar
19 Paul S. Gupta V. Gupta R. Loupy A. Tetrahedron Lett. 2003, 44: 439 ; and references cited therein

Crossref Google Scholar
20 Paul S. Nanda P. Gupta R. Loupy A. Tetrahedron Lett. 2002, 43: 4261

Crossref Google Scholar
21 Paul S. Nanda P. Gupta R. Molecules 2003, 8: 374

Crossref Google Scholar
22a Loupy A. Modern Solvents in Organic Synthesis In Topics in Current Chemistry 1999, 206: 153

Crossref Google Scholar
22b Tanaka K. Toda F. Chem. Rev. 2000, 100: 1025

Crossref Google Scholar
22c Tanaka K. Solvent-free Organic Synthesis Wiley-VCH; Weinheim: 2003.

Crossref Google Scholar
23 Walkiewicz JW. Kazonich G. McGill SL. Miner. Met. Process 1988, 5: 39

Google Scholar
24 Olah GA. In Friedel-Crafts and Related Reactions Vol. III: Interscience; New York: 1964. p.10

Google Scholar
25a Perreux L. Loupy A. Tetrahedron 2001, 57: 9199

Crossref Google Scholar
25b Perreux L. Loupy A. Delmotte M. Tetrahedron 2003, 59: 2185

Crossref Google Scholar