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Volumn , Issue 4, 1999, Pages 603-606

A new convenient Friedel-Crafts alkylation of aromatic compounds with secondary alcohol methanesulfonates in the presence of scandium(III) trifluoromethanesulfonate or trifluoromethanesulfonic acid as the catalyst

Author keywords

Aromatic compounds; Friedel Crafts alkylation; Scandium(III) triflate; Secondary alcohol methanesulfonates; Triflic acid

Indexed keywords

ALKYLATING AGENT; AROMATIC COMPOUND; MESYLIC ACID DERIVATIVE; SCANDIUM(III) TRIFLUOROMETHANESULFONATE; SECONDARY ALCOHOL METHANESULFONATE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

EID: 0032917310     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3436     Document Type: Article
Times cited : (21)

References (42)
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    • The contaminating methanesulfonic acid was removed by decantation
    • The contaminating methanesulfonic acid was removed by decantation.
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    • Even at room temperature anisole could react slowly with la under the TfOH-catalyzed conditions (6 h, 79% yield of 2h), but no significant improvement in regioselectivity was observed (o: p = 59: 41)
    • Even at room temperature anisole could react slowly with la under the TfOH-catalyzed conditions (6 h, 79% yield of 2h), but no significant improvement in regioselectivity was observed (o: p = 59: 41).
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    • 3-catalyzed Friedel-Crafts acylation of anisoles proceeds in quite high yields. See for example: Kawada, A.; Mitamura, S.; Kobayashi, S. Synlett 1994, 545. Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. Kobayashi, S.; Moriwaki, M.; Hachiya, I. J. Chem. Soc., Chem. Commun. 1995, 1527. Kawada, A.; Mitamura, S.; Kobayashi, S. Chem. Commun. 1996, 183. Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett 1996, 171. Kobayashi, S.; Moriwaki, M.; Hachiya, I. Bull. Chem. Soc. Jpn. 1997, 70, 267.
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    • 3-catalyzed Friedel-Crafts acylation of anisoles proceeds in quite high yields. See for example: Kawada, A.; Mitamura, S.; Kobayashi, S. Synlett 1994, 545. Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. Kobayashi, S.; Moriwaki, M.; Hachiya, I. J. Chem. Soc., Chem. Commun. 1995, 1527. Kawada, A.; Mitamura, S.; Kobayashi, S. Chem. Commun. 1996, 183. Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett 1996, 171. Kobayashi, S.; Moriwaki, M.; Hachiya, I. Bull. Chem. Soc. Jpn. 1997, 70, 267.
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    • 3-catalyzed Friedel-Crafts acylation of anisoles proceeds in quite high yields. See for example: Kawada, A.; Mitamura, S.; Kobayashi, S. Synlett 1994, 545. Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. Kobayashi, S.; Moriwaki, M.; Hachiya, I. J. Chem. Soc., Chem. Commun. 1995, 1527. Kawada, A.; Mitamura, S.; Kobayashi, S. Chem. Commun. 1996, 183. Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett 1996, 171. Kobayashi, S.; Moriwaki, M.; Hachiya, I. Bull. Chem. Soc. Jpn. 1997, 70, 267.
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    • 3-catalyzed Friedel-Crafts acylation of anisoles proceeds in quite high yields. See for example: Kawada, A.; Mitamura, S.; Kobayashi, S. Synlett 1994, 545. Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. Kobayashi, S.; Moriwaki, M.; Hachiya, I. J. Chem. Soc., Chem. Commun. 1995, 1527. Kawada, A.; Mitamura, S.; Kobayashi, S. Chem. Commun. 1996, 183. Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett 1996, 171. Kobayashi, S.; Moriwaki, M.; Hachiya, I. Bull. Chem. Soc. Jpn. 1997, 70, 267.
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    • 3-catalyzed Friedel-Crafts acylation of anisoles proceeds in quite high yields. See for example: Kawada, A.; Mitamura, S.; Kobayashi, S. Synlett 1994, 545. Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153. Kobayashi, S.; Moriwaki, M.; Hachiya, I. J. Chem. Soc., Chem. Commun. 1995, 1527. Kawada, A.; Mitamura, S.; Kobayashi, S. Chem. Commun. 1996, 183. Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett 1996, 171. Kobayashi, S.; Moriwaki, M.; Hachiya, I. Bull. Chem. Soc. Jpn. 1997, 70, 267.
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    • Only a complex hydrocarbon mixture was obtained
    • Only a complex hydrocarbon mixture was obtained.
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    • 3-catalyzed reactions. However, this can be precluded based on the following reasons: (1) the less amount of TfOH tends significantly to lower its catalytic activity (Table 1, entry 10), (2) hydrolysis of lanthanide compounds is very slow (see reference 3)
    • 3-catalyzed reactions. However, this can be precluded based on the following reasons: (1) the less amount of TfOH tends significantly to lower its catalytic activity (Table 1, entry 10), (2) hydrolysis of lanthanide compounds is very slow (see reference 3).
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