Abstract
Indium triflate [In(OTf)3] was found to be excellent catalyst (0.5 or 2.0 mol%) for the mononitration of aromatic compounds using a single equivalent of nitric acid (60 or 90%, 1.0 equiv.) without using a halogenated solvent. The side product is water and the indium triflate catalyst can be readily recovered from the aqueous phase and reused.
References
1.
Ingold C.K.
, Structure and Mechanism in Organic Chemistry 2nd edn, Cornell University Press , Ithaca, New York , 1969 .
2.
Olah G.A.
, and
Kuhn S.J.
, in Friedel-Crafts and Related Reactions , Wiley-Interscience , New York , Vol. 2 , 1964 .
3.
Olah G.A.
, ACS Symp. Series, Vol. 22.
Albright F.
, ed., Washington DC , 1967 .
4.
Hoggett J.G.
,
Moodie R.B.
,
Penton J.R.
, and
Schofield K.
, Nitration and Aromatic Reactivity , Cambridge University Press , London , 1971 .
5.
Schofield K.
, Aromatic Nitration, Cambridge University Press , London , 1980 .
6.
Olah G.A.
,
Malhotra R.
, and
Narang S.C.
, Nitration: Methods and Mechanism ,
Feuer H.
, ed., VCH Publishers , New York , 1989 .
7.
Malysheva L.V.
,
Paukshtis E.A.
, and
Ione K.G.
, Catal. Rev. Sci. Eng. , 1995 , 37 , 179 .
8.
Cornelis A.
,
Laszlo P.
, and
Pennetreau P.
, Bull. Soc. Chim. Belg. , 1984 , 961 .
9.
Laszlo P.
, and
Pennetreau P.
, J. Org. Chem. , 1987 , 52 , 2407 .
10.
Kwok T.J.
, and
Jayasuriya K.
, J. Org. Chem. , 1994 , 59 , 4939 .
11.
Smith K.
,
Musson A.
, and
Deboos G.A.
, J. Org. Chem. , 1998 , 63 , 8448 .
12.
Samajdar S.
,
Becker F.F.
, and
Banik B.K.
, Tetrahedron Lett. , 2000 , 41 , 8017 .
13.
Waller F.J.
,
Barrett A.G.M.
,
Braddock D.C.
, and
Ramprasad D.
, Tetrahedron Lett. , 1998 , 39 , 1641 –1642 .
14.
Waller F.J.
,
Barrett A.G.M.
,
Braddock D.C.
, and
Ramprasad D.
, Chem. Commun. , 1997 , 613 .
15.
Barrett A.G.M.
,
Braddock D.C.
,
Ducray R.
,
McKinnell R.M.
, and
Waller F.J.
, Synlett , 2001 , 57 .
16.
Waller F.J.
,
Barrett A.G.M.
,
Braddock D.C.
,
McKinnell R.M.
, and
Ramprasad D.
, J. Chem. Soc., Perkin Trans. 1 , 1999 , 867 .
17.
Waller F.J.
,
Barrett A.G.M.
,
Braddock D.C.
,
McKinnell R.M.
,
White A.J.P.
,
Williams D.J.
, and
Ducray R.
, J. Org. Chem. , 1999 , 64 , 2910 .
18.
Frost C.G.
,
Hartley J.P.
, and
Griffin D.
, Tetrahedron Lett. , 2002 , 43 , 4789 .
19.
Chauhan K.K.
,
Frost C.G.
,
Love I.
, and
Waite D.
, Synlett , 1999 , 1743 .
20.
Loh T.P.
,
Pei J.
, and
Lin M.
, Chem. Commun. , 1996 , 2315 .
21.
Ali T.
,
Chauhan K.K.
, and
Frost C.G.
, Tetrahedron Lett. , 1999 , 40 , 5621 .
22.
Babu G.
, and
Perumal T.
, Tetrahedron , 1998 , 54 , 1627 .
23.
Babu G.
, and
Perumal T.
, Tetrahedron Lett. , 1998 , 39 , 3225 .
24.
Loh T.P.
, and
Wei L.-L.
, Synlett , 1998 , 975 .
25.
Loh T.-P.
, and
Wei L.-L.
, Tetrahedron , 1998 , 54 , 7615 .
26.
Mukaiyama T.
,
Ohno J.S.
,
Han J.S.
, and
Kobayashi S.
, Chem. Lett. , 1991 , 949 .
27.
Sobhana Babu B.
, and
Balasubramanian K.K.
, Tetrahedron Lett. , 2000 , 41 , 113 .
28.
Miyai T.
,
Ueba M.
, and
Baba A.
, Synlett , 1999 , 182 .
29.
Miyai T.
,
Onishi Y.
, and
Baba A.
, Tetrahedron , 1999 , 55 , 1017 .
30.
Miyai T.
,
Inoue K.
,
Yasuda M.
, and
Baba A.
, Tetrahedron Lett. , 1998 , 39 , 1929 .
31.
Inoue K.
,
Yasuda M.
,
Shibata I.
, and
Baba A.
, Tetrahedron Lett. , 2000 , 41 , 113 .
32.
Forsberg J.H.
,
Spasiano V.T.
,
Balasubramanian T.M.
,
Liu G.K.
,
Kinsley S.A.
,
Duckworth C.A.
,
Poteruca J.J.
,
Brown P.S.
, and
Miller J.L.
, J. Org. Chem. , 1987 , 52 , 1017 .
