6644
B. Ganchegui et al. / Tetrahedron Letters 43 (2002) 6641–6644
3. Bouquillon, S.; Ganchegui, B.; Estrine, B.; He´nin, F.;
11. For a Wacker-type reaction, see: Namboodiri, V. V.;
Varma, R. S.; Sahle-Demessie, E.; Pillai, U. R. Green
Chem. 2002, 4, 170–173.
12. In other solvents, the addition of an inorganic base is
often required to obtain an efficient process.4a,6,7
13. (bmim)(PF6): 1-butyl-3-methylimidazolium hexafluoro-
phosphate.
14. Keresszegi, C.; Mallat, T.; Baiker, A. New J. Chem. 2001,
25, 1163–1167.
15. Murahashi, S.; Shimura, T.; Moritani, I. Chem. Commun.
1974, 931–932.
16. Typical experiment, run 11. A round-bottomed flask (10
ml) equipped with a magnetic stir bar and reflux con-
denser was charged with PdCl2 (5 mg, 0.03 mmol) and
n-Bu4NBr (1.5 g). The system was connected to a vac-
uum/argon line and the flask was heated under vacuum
at 120°C (oil bath) for 2 h. After switching to the argon
line, indan-1-ol (134 mg, 1 mmol) was introduced and the
temperature of the oil bath was maintained at 120°C for
22 h. After removing the oil bath, diethyl ether (5 ml) was
added by the top of the condenser. The mixture was
stirred for a few minutes and then poured on a sintered-
glass frit. The flask was washed with diethyl ether and the
solid carefully triturated with the same solvent (2 ml×5).
GC analysis (capillary column HP-Innowax, 170°C, dec-
9-en-1-ol as internal standard) of the solution showed the
complete conversion of the substrate and the formation
of indan-1-one (95%).
Muzart, J. J. Organomet. Chem. 2001, 634, 153–156.
4. (a) A¨ıt-Mohand, S.; He´nin, F.; Muzart, J. Tetrahedron
Lett. 1995, 36, 2473–2476; (b) A¨ıt-Mohand, S.; Muzart, J.
J. Mol. Catal. A: Chem. 1998, 129, 135–139; (c) Bouquil-
lon, S.; He´nin, F.; Muzart, J. Organometallics 2000, 19,
1434–1437; (d) Rothenberg, G.; Humbel, S.; Muzart, J. J.
Chem. Soc., Perkin Trans. 2 2001, 1998–2004.
5. (a) Llyod, W. G. J. Org. Chem. 1967, 32, 2816–2819; (b)
Kaneda, K.; Fujii, M.; Moriaka, K. J. Org. Chem. 1996,
61, 4502–4503; (c) Bortolo, R.; Bianchi, D.; D’Alosio, R.;
Querci, C.; Ricci, M. J. Mol. Catal. A: Chem. 2000, 153,
25–29; (d) Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J.
Am. Chem. Soc. 2001, 123, 7475–7476; (e) Ferreira, E.
M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725–
7726; (f) Kakiuchi, N.; Maeda, Y.; Nishimura, T.;
Uemura, S. J. Org. Chem. 2001, 66, 6620–6625.
6. (a) Blackburn, T. F.; Schwartz, J. S. Chem. Commun.
1977, 157–158; (b) Peterson, K. P.; Larock, R. C. J. Org.
Chem. 1998, 63, 3185–3189; (c) Hallman, K.; Moberg, C.
Adv. Synth. Cat. 2001, 343, 260–263.
7. ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A.
Science 2000, 287, 1636–1639.
8. (a) Howarth, J. Tetrahedron Lett. 2000, 41, 6627–6629;
(b) Song, C. E.; Roh, E. J. Chem. Commun. 2000, 837–
838; (c) Owens, G. S.; Abu-Omar, M. M. Chem. Com-
mun. 2000, 1165–1166; (d) Gaillon, L.; Bedioui, F. Chem.
Commun. 2001, 1458–1459; (e) Singer, R. D.; Scammells,
P. J. Tetrahedron Lett. 2001, 42, 6831–6833.
9. The addition of tetraalkylammonium salts in ruthenium-
catalyzed oxidations of alcohols has allowed the recovery
of the catalyst but methylene chloride was used as sol-
vent. See: Ley, S. V.; Ramarao, C.; Smith, M. D. Chem.
Commun. 2001, 2278–2279.
17. Rao, V. S.; Perlin, A. S. J. Org. Chem. 1982, 47, 367–369.
18. Low amounts of 2 were also obtained from a DMF
solution of 1 heated at 120°C for 21 h (Conv.: 9%, yield:
7%).
19. We have already obtained PhCO2n-Bu from (PhCO)2O
and n-Bu4NBr.3
20. The formation of esters from aldehyde insertion into
rhodium–alkoxide complexes and subsequent b-H elimin-
ation has been recently reported. See: Krug, C.; Hartwig,
J. F. J. Am. Chem. Soc. 2002, 124, 1674–1679.
10. (a) Farmer, V.; Welton, T. Green Chem. 2002, 4, 97–102;
(b) Seddon, K. R.; Stark, A. Green Chem. 2002, 4,
119–123; (c) Ansari, I. A.; Gree, R. Org. Lett. 2002, 4,
1507–1509.