Abstract
A mild and highly efficient method has been developed for the deprotection of 1,1-diacetates using a catalytic amount of indium tribromide immobilised in 1-butyl-3-methylimidazolium hexafluorophosphate as an ionic liquid. This affords the corresponding the parent aldehydes in excellent yields. The recovered ionic liquid containing catalyst has been recycled in three subsequent runs.
References
1.
(a)
Poliakoff M.
,
Fitzpatrick J. M.
,
Farren T. R.
, and
Anastas P. T.
, Science , 2002 , 297 , 807 .
2.
Desimone J.M.
, Science , 2002 , 297 , 799 .
3.
Dogers R.D.
, and
Seddon K. R.
, Science , 2003 , 302 , 792 .
4.
(a)
Welton T.
, Chem. Rev. , 1999 , 99 , 2071 .
5.
Wasserscheid P.
, and
Keim W.
, Angew. Chem., Int. Ed. , 2000 , 39 , 3773 .
6.
Earle M.J.
, and
Seddon K. R.
, Pure. Appl. Chem. , 2000 , 72 , 1391 .
7.
Greene T.W.
, and
Wuts P. G. M.
, Protecting Groups in Organic Chemistry , Wiley & Sons , New York , 3rd edn., 1999 .
8.
(a)
Aggen D.H.
,
Arnold J. N.
,
Hayes P. D.
,
Smoter N. J.
, and
Mohan R. S.
, Tetrahedron , 2004 , 60 , 3675 .
9.
Chakraborti A.K.
,
Thilagavathi R.
, and
Kumar R.
, Synthesis , 2004 , 831 .
10.
Ghosh R.
,
Maiti S.
,
Chakraborty A.
, and
Halder R.
, J. Mol. Catal. A: Chem. , 2004 , 215 , 49 .
11.
Jin T.-S.
,
Feng G.-L.
,
Yang M.-N.
, and
Li T.-S.
, Synth. Commun. , 2004 , 34 , 1645 .
12.
Heerden F.R.
,
Huyser J. J.
,
Williams D. B. G.
, and
Holzapfer C. W.
, Tetrahedron Lett. , 1998 , 39 , 5281 .
13.
Trost B.M.
, and
Lee C.
, J. Am. Chem. Soc. , 2001 , 123 , 12191 .
14.
Angelis Y.S.
, and
Smonou I.
, Tetrahedron Lett. , 1998 , 39 , 2823 .
15.
Tsang S.M.
,
Wood E. H.
, and
Johnson J. R.
, Org. Synth. Coll. , 1955 , 3 , 641 .
16.
Lieberman S.V.
, and
Connor R.
, Org. Synth. Coll. , 1951 , 2 , 441 .
17.
(a)
Li T.-S.
,
Zhang Z.-H.
, and
Fu C.-G.
, Tetrahedron Lett. , 1997 , 38 , 3285 .
18.
Perez E.R.
,
Marrero A. L.
,
Perez R.
, and
Autie M. A.
, Tetrahedron Lett. , 1995 , 36 , 1779 .
19.
Villemin D.
, and
Martin B.
, J. Chem. Research. (S) , 1994 , 146 .
20.
Jin T.-S.
,
Ma Y.-R.
,
Zhang Z.-H.
, and
Li T.-S.
, Synth. Commun. , 1997 , 27 , 3379 .
21.
Ballini R.
,
Bordoni M.
,
Bosica G.
,
Maggi R.
, and
Sartori G.
, Tetrahedron Lett. , 1998 , 39 , 7587 .
22.
Narayana C.
,
Padmanabhan S.
, and
Kabalka G. W.
, Tetrahedron Lett. , 1990 , 31 , 6977 .
23.
Cotelle P.
, and
Catteau J.-P.
, Tetrahedron Lett. , 1992 , 33 , 3855 .
24.
Varma R.S.
,
Chatterjee A. K.
, and
Varma M.
, Tetrahedron Lett. , 1993 , 34 , 3207 .
25.
Reddy G.S.
,
Radhika R.
,
Neelakantan P.
, and
Iyengar D. S.
, Ind. J. Chem. , 2002 , 41B , 863 .
26.
Ramalingam T.
,
Srinivas R.
,
Reddy B. V. S.
, and
Yadav J. S.
, Synth. Commun. , 2001 , 31 , 1091 .
27.
Zolifgol M.A.
,
Zebarjadian M. H.
,
Mohammadpoor-Baltork I.
, and
Shamsipur M.
, Synth. Commun. , 2002 , 32 , 2803 .
28.
Mohammadpoor-Baltork I.
, and
Alyan H.
, J. Chem. Research. (S) , 1999 , 272 .
29.
Mohammadpoor-Baltork I.
, and
Aliyan H.
, Synth. Commun. , 1999 , 29 , 2741 .
30.
Curini M.
,
Epifano F.
,
Marcotullio M. C.
,
Rosati O.
, and
Nocchetti M.
, Tetrahedron Lett. , 2002 , 43 , 2709 .
31.
Aggarwai V.
,
Fonquerna S.
, and
Vennall G. P.
, Synlett , 1998 , 849 .
32.
Kochhar K.S.
,
Bal B. S.
,
Deshpande R. P.
,
Rajadhyaksha S. N.
, and
Pinnick H. W.
, J. Org. Chem. , 1983 , 48 , 1765 .
33.
Ku Y.Y.
,
Patel R.
, and
Sawick D.
, Tetrahedron Lett. , 1993 , 34 , 8037 .
34.
Reddy M.A.
,
Reddy L. R.
,
Bhanumathi N.
, and
Rao K. R.
, Synth. Commun. , 2002 , 32 , 273 .
35.
(a)
Li C.J.
, and
Chan T. H.
, Tetrahedron , 1999 , 55 , 11149 .
36.
Babu G.
, and
Perumal P. T.
, Aldrichimica Acta , 2000 , 33 , 16 .
37.
Chauhan K. K.
, and
Frost C. G.
, J. Chem. Soc., Perkin Trans. 1 , 2000 , 3015 .
38.
(a)
Fu N-Y.
,
Yuan Y. H.
,
Cao Z.
,
Wang S.-W.
,
Wang J.-T.
, and
Peppe C.
, Tetrahedron , 2002 , 58 , 4801 .
39.
Yadav J.S.
,
Reddy B. V. S.
,
Krishna A. D.
, and
Swamy T.
, Tetrahedron Lett. , 2003 , 44 , 6055 .
40.
Agnusdei M.
,
Bandini M.
,
Melloni A.
, and
Umani-Ronchi A.
, J. Org. Chem. , 2003 , 68 , 7126 .
41.
Yadav J.S.
,
Reddy B. V. S.
, and
Baishya G.
, Synlett , 2003 , 396 .
42.
Yadav J. S.
,
Reddy B. V. S.
, and
Swamy T.
, Synthesis , 2004 , 106 .
43.
Weast R.C.
, and
Grasselli J. G.
, Handbook of Date on Organic Compounds , CRC Press Inc. , Boca Raton, Florida , 2nd edn, 1989 .
44.
Heilbron I.
, and
Bunbury H. M.
, Dictionary of Organic Compounds , Eyre & Spottiswoode , London , 1953 .
45.
Yin L.
,
Zhang Z.-H.
,
Wang Y.-M.
, and
Pang M.-L.
, Synlett , 2004 , 1727 .