E. Quesada et al. / Tetrahedron 62 (2006) 6673–6680
6679
3
0
(
.3.4. 1-Ethynyl-2-bromobenzene (Table 3, entry iv).
.30 mmol scale, oxidation time of 4 h; chromatography
10% EtOAc/PE) afforded the title compound (51 mg,
4. Colvin, E. W.; Hamill, B. J. J. Chem. Soc., Perkin Trans. 1
1977, 869–874.
5. Brown, D. G.; Velthuisen, E. J.; Commerford, J. R.; Brisbois,
R. G.; Hoye, T. R. J. Org. Chem. 1996, 61, 2540–2541.
6. Ohira, S. Synth. Commun. 1989, 19, 561–564.
9
scopic data consistent with those reported in the literature.
4%) as a colourless oil; R 0.72 (50% EtOAc/PE); spectro-
f
3
8
7
. Roth, G. J.; Liepold, B.; M u¨ ller, S. G.; Bestmann, H. J. Synlett
996, 521–522.
. (a) Callant, P.; D’Haenens, L.; Vandewalle, M. Synth. Commun.
984, 14, 155–161; (b) Ghosh, A. K.; Bischoff, A.; Cappiello, J.
3
.3.5. Phenylacetylene (Table 3, entry v). 10 mmol scale,
1
oxidation time of 4 h; distillation from the crude reaction
mixture gave the title compound (890 mg, 87%) as a colour-
less oil; spectroscopic data consistent with those reported in
8
1
Eur. J. Org. Chem. 2003, 821–832.
. Dixon, D. J.; Ley, S. V.; Reynolds, D. J. Chem.—Eur. J. 2002, 8,
3
9
the literature.
9
1
621–1636; Goundry, W. R. F.; Baldwin, J. E.; Lee, V.
3
0
.3.6. 1-Ethynyl-4-methoxybenzene (Table 3, entry vi).
.36 mmol scale, oxidation time of 4 h; chromatography
Tetrahedron 2003, 59, 1719–1729; Xu, Z.; Peng, Y.; Ye, T.
Org. Lett. 2003, 5, 2821–2824; Marshall, J. A.; Schaaf, G. M.
J. Org. Chem. 2003, 68, 7428–7432; Maehr, H.; Uskokovic,
M. R. Eur. J. Org. Chem. 2004, 1703–1713.
(10% EtOAc/PE) gave the title compound (27 mg, 56%)
as a white waxy solid; R 0.76 (50% EtOAc/PE); spectro-
scopic data consistent with those reported in the literature.
f
4
0
1
2
0. For a review of the use of MnO in tandem oxidation processes
see: Taylor, R. J. K.; Reid, M.; Foot, J.; Raw, S. A. Acc. Chem.
Res. 2005, 38, 851–869 and references therein; see also
Refs. 12, 14, 25 and 27 and McAllister, G. D.; Oswald, M.
F.; Paxton, R. J.; Raw, S. A.; Taylor, R. J. K. Tetrahedron
2006, 62, doi:10.1016/j.tet.2005.12.078.
3.3.7. 1-Ethynyl-2,4-dimethoxybenzene (Table 3, entry
vii). 0.33 mmol scale, oxidation time of 8 h; chromato-
graphy (10% EtOAc/PE) gave the title compound (31 mg,
9%) as a colourless oil; R 0.6 (50% EtOAc/PE); spectro-
f
5
scopic data consistent with those reported in the literature.
4
1
1
1
1
1. Baxendale, I. R.; Ley, S. V.; Sneddon, H. F. Synlett 2002,
7
75–777.
2. Preliminary communication: Raw, S. A.; Reid, M.; Roman, E.;
Taylor, R. J. K. Synlett 2004, 819–822.
3
.3.8. 1-Naphthylacetylene (Table 3, entry viii). 0.23 mmol
scale, oxidation time of 4 h; chromatography (10% EtOAc/
PE) gave the title compound (31 mg, 89%) as a colourless
oil; R 0.65 (50% EtOAc/PE); spectroscopic data consistent
3. (a) Dolhem, F.; Li e` vre, C.; Demailly, G. Tetrahedron Lett.
f
4
2
2002, 43, 1847–1849; (b) Patrick, M.; Gennet, D.; Rassat, A.
Tetrahedron Lett. 1999, 40, 8575–8578.
with those reported in the literature.
3
0
.3.9. 1-Ethynyl-4-phenylbenzene (Table 3, entry ix).
.20 mmol scale, oxidation time of 4 h; chromatography
14. Blackburn, L.; Pei, C.; Taylor, R. J. K. Synlett 2002, 215–218;
Reid, M.; Rowe, D. J.; Taylor, R. J. K. Chem. Commun. 2003,
2284–2285.
15. Simoni, D.; Rossi, M.; Rondanin, R.; Mazzani, A.; Baruchello,
C.; Malagutti, C.; Roberti, M.; Indiviata, F. P. Org. Lett. 2000,
(10% EtOAc/PE) gave the title compound (33 mg, 92%)
as a colourless oil; R 0.6 (50% EtOAc/PE); spectroscopic
data consistent with those reported in the literature.
f
4
3
2, 3765–3768.
3
.3.10. 3-Ethynyl pyridine (Table 3, entry x). 0.50 mmol
1
6. Magnuson, S. R. Tetrahedron 1995, 51, 2167–2213; for recent
examples of two directional synthesis using TOPs see: Wei, X.;
Taylor, R. J. K. J. Org. Chem. 2000, 65, 616–620; Frederico,
D.; Donate, P. M.; Constantino, M. G.; Bronze, E. S.; Sairre,
M. I. J. Org. Chem. 2003, 68, 9126–9128; McDermott, P. J.;
Stockman, R. A. Org. Lett. 2005, 7, 27–29.
scale, oxidation time of 10 h; chromatography (10%
EtOAc/PE) gave the title compound (35 mg, 68%) as a white
waxy solid; R 0.5 (EtOAc); spectroscopic data consistent
f
4
4
with those reported in the literature.
3
0
.3.11. Buta-1,3-diynyl-benzene (Table 3, entry xi).
.50 mmol scale, oxidation time of 24 h; chromatography
1
1
1
7. Bestmann, H. J.; Frey, H. Liebigs Ann. Chem. 1980, 12, 2061–
2
071.
8. Lok, W. N.; Ward, A. D. Aust. J. Chem. 1978, 31, 617–
25.
(
10% EtOAc/PE) gave the title compound (37 mg, 59%)
as a colourless liquid; R 0.75 (EtOAc); spectroscopic data
f
6
4
5
consistent with those reported in the literature.
9. For some noteworthy recent examples in natural product syn-
thesis see: Roush, W. R.; Brown, B. B. J. Org. Chem. 1993,
Acknowledgements
58, 2162–2172; Myers, A. G.; Hogan, P. C.; Hurd, A. R.;
Goldberg, S. D. Angew. Chem., Int. Ed. 2002, 41, 1062–
We aregrateful to theEPSRC forpostdoctoral support(ROPA
Fellowship, S.A.R.), to the EPSRC, Oxford Chemicals and
The Gen Foundation for studentship support (M.R.), and to
ENSIACET, Toulouse for exchange support (E.R.).
1
067; Evans, D. A.; Starr, J. T. Angew. Chem., Int. Ed. 2002,
1, 1787–1790; Mergott, D. J.; Frank, S. A.; Roush, W. R.
4
Org. Lett. 2002, 4, 3157–3160.
2
2
2
0. Uenishi, J.; Kawahama, R.; Yonemitsu, O. J. Org. Chem. 1998,
6
3, 8965–8975.
1. Kuang, C.; Senboku, H.; Tokuda, M. Tetrahedron 2002, 58,
1491–1496.
References and notes
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1
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3
3