Abstract
The Friedel–Crafts acylation of 1-naphthol and phenol derivatives with carboxylic acids were investigated by using a catalytic amount of metal-triflate, in particular Yb(OTf)3, under solvent-free conditions. Both aliphatic and aromatic carboxylic acids reacted easily to afford the corresponding hydroxyaryl ketones.
References
1.
Olah G.A.
Friedel–Crafts and related reactions , Wiley-Interscience , New York , 1964 , Vol. III , part 1.
2.
Prakash G.K. S.
,
Panja C.
,
Mathew T.
, and
Olah G. A.
, Catal. Lett. , 2007 , 114 , 24 .
3.
Choudary B.M.
,
Ranganath K. V. S.
,
Yadav J.
, and
Kantam M. L.
, Tetrahedron Lett. , 2005 , 46 , 1369 .
4.
Dao T.T.
,
Chi Y. S.
,
Kim H. P.
,
Kim S.
, and
Park H.
, Bioorg. Med. Chem. Lett. , 2004 , 14 , 1165 .
5.
Veverkova E.
,
Meciarova M.
,
Gotov B.
, and
Toma S.
, Green Chem. , 2002 , 4 , 361 .
6.
Takanishi Y.
,
Ouchi Y.
,
Takezoe H.
,
Fukuda A.
,
Mochizuki A.
, and
Nakatsuka M.
, Mol. Cryst. Liq. Cryst. , 1991 , 199 , 111 .
7.
March J.
, Advanced organic chemistry , 5th edn. Wiley , New York , 2001 p.725 .
8.
Martin R.
, Org. Prep. Proc. Int. , 1992 , 24 , 369 .
9.
Bensari A.
, and
Zaveri N. T.
, Synthesis , 2003 , 267 .
10.
Sartori G.
,
Casnati G.
, and
Bigi F.
, J. Org. Chem. , 1990 , 55 , 4371 .
11.
Kozhevnikov I.V.
, Appl. Catal, A , 2003 , 256 , 3 .
12.
Pandey A.K.
, and
Singh A. P.
, Catal. Lett , 1997 , 44 , 129 .
13.
Firouzabadi H.
,
Iranpoor N.
, and
Nowrouzi F.
, Tetrahedron Lett. , 2003 , 44 , 5343 .
14.
Chiche B.
,
Finiels A.
,
Gautheir C.
, and
Geneste P.
, J. Mol. Catal , 1987 , 42 , 229 .
15.
Ranu B.C.
,
Ghosh K.
, and
Jana U.
, J. Org. Chem. , 1996 , 61 , 9546 .
16.
Sarvari M.H.
, and
Sharghi H.
, Synthesis , 2004 , 2165 .
17.
Kawamura M.
,
Cui D. M.
,
Hayashi T.
, and
Shimada S.
, Tetrahedron Lett. , 2003 , 44 , 7715 .
18.
Gmouth S.
,
Yang H.
, and
Vaultier M.
, Org. Lett. , 2003 , 5 , 2219 .
19.
Paul S.
, and
Gupta M.
, Synthesis , 2004 , 1789 .
20.
Vijayakumar B.
,
Iyengar P.
,
Nagendrappa G.
, and
Prakash B. S. J.
, Indian J. Chem., Sect B , 2005 , 9 , 1950 .
21.
Khalafi N.A.
,
Parhami A.
,
Zare A.
, and
Zare A. R. M.
, J. Iran. Chem. Soc. , 2008 , 3 , 413 .
22.
Prasad A.K.
,
Kumar V.
,
Malhotra S.
,
Ravikumar V. T.
,
Sanghvi Y. S.
, and
Parmar V. S.
, Bioorg. Med. Chem. , 2005 , 13 , 4467 .
23.
Klamann E.
,
Shternov V. A.
, and
Gates L. W.
, J. Am. Chem. Soc. , 1933 , 55 , 2576 .
24.
Nummert V
,
Piirsalu M.
,
Maemets V.
, and
Koppel I.
, J. Phys. Org. Chem. , 2005 , 18 , 1138 .
25.
Cruickshank J.H.
, and
Robinson R.
, J. Chem. Soc. , 1938 , 2064 .
26.
Li W.M.
,
Lai H. Q.
,
Ge Z. H.
,
Ding C. R.
, and
Zhou Y.
, Synth. Commun. , 2007 , 37 , 1595 .
27.
Zhong T.S.
, and
Huang M. L.
, Huaxue Xuebao , 1981 , 3 , 229 .
28.
Fawaz G.
,
Fieser L. F.
, and
Harvard U.
, J. Am. Chem. Soc. , 1950 , 72 , 996 .
29.
Cheema U.S.
, and
Venkataraman K.
, J. Chem. Soc. , 1932 , 918 .
30.
Park K.K.
, and
Jeong J.
, Tetrahedron , 2005 , 61 , 545 .
31.
Klarmann E.
, J. Am. Chem. Soc. , 1926 , 48 , 2358 .
32.
Booth B.L.
,
Haszeldine R. N.
, and
Laali K.
, J. Chem. Soc., Perkin Trans. 1 , 1980 , 2887 .
33.
Gadgil V.
, and
Harichian B.
, WO 2004080939 , 2004 , CAN 141:297651.
34.
Tomita M.
,
Uyeo S.
,
Kobayashi S.
,
Koizumi J.
, and
Tamura K.
, Yakugaku Zasshi , 1949 , 69 , 149 .
35.
Shah H.A.
, and
Shah R. C.
, J. Chem. Soc. , 1940 , 245 .
36.
Kenkyusho S.
, JP 59175448A , 1984 , CAN 102:113043.
