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Yu, N.; Fang, Z.; Yang, L.; Shi, Z. J. Am. Chem. Soc. 2005,
27, 18004–18005; (c) Mu, R.; Liu, Z.; Yang, Z.; Liu, Z.;
Wu, L.; Liu, Z.-L. Adv. Synth. Catal. 2005, 347, 1333–1336;
d) Schultz, M. J.; Hamilton, S. S.; Jensen, D. R.; Sigman,
2
a pyrex glass test tube fitted with an O -balloon was stirred
1
and irradiated at rt with a 500 W xenon lamp externally for
the indicated time. The reaction mixture was concentrated
under reduced pressure, and 10% NaOH aq solution was
(
M. S. J. Org. Chem. 2005, 70, 3343–3352; (e) Liu, R.; Liang,
X.; Dong, C.; Hu, X. . J. Am. Chem. Soc. 2004, 126, 4112–
2
added. The aqueous solution was washed with Et O, and
then acidified with 6% HCl aq solution, which was
4113; (f) Mori, K.; Hara, T. i.; Mizugaki, T.; Ebitani, K.;
extracted with Et O. The organic layer was washed with
2
Kaneda, K. J. Am. Chem. Soc. 2004, 126, 10657–10666; (g)
Marko, I. E.; Gautier, A.; Dumeunier, R.; Doda, K.;
Philippart, F.; Brown, S. M.; Urch, C. J. Angew. Chem., Int.
Ed. 2004, 43, 1588–1591; (h) Stahl, S. S. Angew. Chem., Int.
Ed. 2004, 43, 3400–3420, and references cited therein; (i)
Iwasawa, T.; Tokunaga, M.; Obora, Y.; Tsuji, Y. J. Am.
Chem. Soc. 2004, 126, 6554–6555; (j) Jensen, D. R.; Schultz,
M. J.; Mueller, J. A.; Sigman, M. S. Angew. Chem., Int. Ed.
2 4
brine and dried over Na SO , and concentrated under
reduced pressure. The product was pure without further
purification. When using secondary alcohol as the sub-
strate, a typical procedure follows: a solution (5 mL) of the
substrate (0.3 mmol) and allylbromide (0.3 equiv) in dry
EtOAc was stirred and irradiated at rt with a 500 W xenon
lamp externally for the indicated time. The reaction mixture
was concentrated under reduced pressure, and 10% NaOH
aq solution was added. The aqueous solution was washed
2003, 42, 3810–3813.
4
5
. (a) Kuwabara, K.; Itoh, A. Synthesis 2006, 1949–1952; (b)
Itoh, A.; Kodama, T.; Hashimoto, S.; Masaki, Y. Synthesis
2
with Et O and the organic layer was concentrated, and the
residue was purified by preparative TLC.
7. Minisci, F.; Porta, O.; Recupero, F.; Punta, C.; Gam-
barotti, C.; Pierini, M.; Galimberti, L. Synlett 2004, 2203–
2205.
8. Aldehydes can be oxidized to the corresponding carboxylic
acids under the same conditions. 4-tert-Butylbenzoic acid
(78%) was obtained when using 4-tert-butylbenzaldehyde as
a substrate.
9. Although we tried to detect the by-product arising from
bromo source by using cinnamyl bromide instead of allyl
bromide, only benzoic acid, which possesses no allyl
residue, was obtained.
2003, 2289–2291.
. (a) Hirashima, S.-I.; Hashimoto, S.; Masaki, Y.; Itoh, A.
Tetrahedron 2006, 62, 7887–7891; (b) Hirashima, S.-I.; Itoh,
A. Synthesis 2006, 1757–1759; (c) Itoh, A.; Hashimoto, S.;
Kodama, T.; Masaki, Y. Synlett 2005, 2107–2109; (d) Itoh,
A.; Hashimoto, S.; Masaki, Y. Synlett 2005, 2639–2640; (e)
Itoh, A.; Hashimoto, S.; Kuwabara, K.; Kodama, T.;
Masaki, Y. Green Chem. 2005, 7, 830–832.
6
. When using primary alcohol as the substrate, a typical
procedure follows: a solution (5 mL) of the substrate
(0.3 mmol) and allyl bromide (0.3 equiv) in dry EtOAc in