DOI: 10.1246/bcsj.73.2325. Friedel-Crafts Reactions Catalyzed by Rare Earth Metal Trifluoromethanesulfonates

Friedel-Crafts Reactions Catalyzed by Rare Earth Metal Trifluoromethanesulfonates

10.1246/bcsj.73.2325

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract Rare earth metal trifluoromethanesulfonates (rare earth metal triflates, RE(OTf)3) were found to be efficient catalysts for Friedel-Crafts acylation and alkylation. In the presence of a catalytic amount of RE(OTf)3, acylation of aromatic compounds having electron-donating substituents such as anisole, thioanisole, and mesitylene with acid anhydrides proceeded smoothly to afford the corresponding aromatic ketones in high yields. Although RE(OTf)3 alone is not effective for acylation of less reactive aromatics such as toluene, the combination of RE(OTf)3 and lithium perchlorate (LiClO4) enhanced the catalytic activity dramatically. Friedel-Crafts acylation reactions using rare earth metal perfluoroalkanesulfonates were also successfully performed in supercritical carbon dioxide (scCO2). Moreover, in the presence of a catalytic amount of RE(OTf)3, aromatic compounds reacted with benzyl chloride smoothly to afford the corresponding alkylation products in high yields. In these reactions, RE(OTf)3 could be easily recovered after the reactions were completed and could be reused without loss of activity.

Bibliography

Kawada, A., Mitamura, S., Matsuo, J., Tsuchiya, T., & Kobayashi, S. (2000). Friedel-Crafts Reactions Catalyzed by Rare Earth Metal Trifluoromethanesulfonates. Bulletin of the Chemical Society of Japan, 73(10), 2325â2333.

Authors 5

Atsushi Kawada (first)
Shuichi Mitamura (additional)
Jun-ichi Matsuo (additional)
Takehiro Tsuchiya (additional)
Shu Kobayashi (additional)

References 103 Referenced 84

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Dates

Type	When
Created	22 years, 11 months ago (Sept. 6, 2002, 6:09 a.m.)
Deposited	1 year, 7 months ago (Jan. 20, 2024, 12:58 a.m.)
Indexed	1 month, 3 weeks ago (July 2, 2025, 2:11 p.m.)
Issued	24 years, 10 months ago (Oct. 1, 2000)
Published	24 years, 10 months ago (Oct. 1, 2000)
Published Online	23 years, 8 months ago (Dec. 27, 2001)
Published Print	24 years, 10 months ago (Oct. 1, 2000)

Funders 0

None

BibTeX

@article{Kawada_2000, title={Friedel-Crafts Reactions Catalyzed by Rare Earth Metal Trifluoromethanesulfonates}, volume={73}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.73.2325}, DOI={10.1246/bcsj.73.2325}, number={10}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Kawada, Atsushi and Mitamura, Shuichi and Matsuo, Jun-ichi and Tsuchiya, Takehiro and Kobayashi, Shu}, year={2000}, month=oct, pages={2325–2333} }

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