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
Synthesis 2003(2): 0267-0271
DOI: 10.1055/s-2003-36822
DOI: 10.1055/s-2003-36822
PAPER
© Georg Thieme Verlag Stuttgart · New York
Titanium(IV) Chloride-Mediated Ortho-Acylation of Phenols and Naphthols
Further Information
Received
17 September 2002
Publication Date:
22 January 2003 (online)
Publication History
Publication Date:
22 January 2003 (online)
Abstract
The use of titanium(IV) chloride as a Lewis acid for direct ortho-acylation of phenols and naphthols proves to be a convenient, more general and direct route to various hydroxyaryl ketones. The route is regioselective, leading to ortho C-acylated products in satisfactory to high yields in most cases.
Key words
ortho-acylation - Lewis acid - electrophilic substitution - hydroxyaryl ketone - regioselectivity
- For reviews on the Fries rearrangement, see
-
1a
Martin R. Org. Prep. Proced. Int. 1992, 24: 369 -
1b See also:
Shine HJ. In Aromatic Rearrangements Elsevier; New York: 1967. p.72 -
1c See also:
Gerecs A. The Fries rearrangement, In Friedel-Crafts and Related Reactions Vol. III:Olah GA. Interscience; New York: 1964. Part 1. p.499 -
2a
Fries K.Finck G. Ber. Dtsch. Chem. Ges. 1908, 41: 4271 -
2b
Fries K.Pfaffendorf W. Ber. Dtsch. Chem. Ges. 1910, 43: 212 -
3a
Martin R.Demerseman P. Synthesis 1989, 25 -
3b
Martin R.Demerseman P. Synthesis 1992, 738 -
3c
Rozenberg V.Danilova T.Sergeeva E.Vorontzov E.Starikova Z.Lysenko K.Belokon Y. Eur. J. Org. Chem. 2000, 3295 - 4
Harroweven DC.Dainty RF. Tetrahedron Lett. 1996, 37: 7659 -
5a The
original work:
Niyazov AN.Namatov B.Atlyev K. Izv. Akad. Nauk Turkm. SSR. Ser. Fiz.-Tekh., Khim. Geol. Nauk. 1974, 62 ; Chem. Abstr. 1975, 82, 170275 -
5b
Trost BM.Saulnier MG. Tetrahedron Lett. 1985, 26: 123 -
5c
Crombie L.Jones RCF.Palmer CJ. Tetrahedron Lett. 1985, 26: 2933 - 6
Sartori G.Gasnati G.Bigi F. J. Org. Chem. 1990, 55: 4371 ; and references cited therein -
7a
Kobayashi S.Moriwaki M.Hachiya I. J. Chem. Soc., Chem. Commun. 1995, 1527 -
7b
Kobayashi S.Moriwaki M.Hachiya I. Synlett 1995, 1153 -
7c
Kobayashi S.Moriwaki M.Hachiya I. Tetrahedron Lett. 1996, 37: 2053 -
7d
Kobayashi S.Moriwaki M.Hachiya I. Bull. Chem. Soc. Jpn. 1997, 70: 267 -
8a For
overviews, see:
Reetz MT. Organotitanium Reagents in Organic Synthesis Springer-Verlag; New York: 1986. -
8b
Reetz MT. Organotitanium Chemistry, In Organometallics in Synthesis 2nd ed.:Schlosser M. Wiley; New York: 2002. - 9
Julia M.Chastrette F. Bull. Chem. Soc. Fr. 1962, 2255