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References and notes
(s, 6H), 2.36 (s, 3H), 7.17 (s, 2H), 7.52–7.70 (m, 9H), 7.80–
.90 (m, 6H).
. Formula C H BBiF , monoclinic, P2 /n, a = 10.206(2) A,
7
˚
6
1
. (a) Kitchin, J. P. In Organic Synthesis by Oxidation with
Metal Compounds; Mijs, W. J., De Jonge, C. R. H. I.,
Eds.; Plenum: New York, 1986, Chapter 15, pp 817–837;
27 26
4
1
˚
˚
b = 17.488(4) A, c = 13.798(3) A, b = 91.0880(10)°, V =
˚
3
ꢁ3
2
462.1(9) A , Z = 4, D
c
= 1.743 g cm , 5432 obsd, 299
variables, R
w
= 0.0526, R = 0.0254 (I > 2.00r(I)), GOF =
(
1
b) Postel, M.; Du n˜ ach, E. Coord. Chem. Rev. 1996, 155,
27; (c) Suzuki, H.; Ikegami, T.; Matano, Y. Synthesis
1
.029. Crystallographic data for the structure of 1a
have been deposited with the Cambridge Crystallo-
graphic Data Centre as Supplementary Publication No.
CCDC 635005. Copies of the data can be obtained, free
of charge, on application to CCDC, 12 Union Road,
Cambridge CB2 1EZ, UK (fax: +44-(0)1223-336033 or
e-mail: deposit@ccdc.cam.ac.uk).
1
997, 249; (d) Komatsu, N. In Organobismuth Chemistry;
Suzuki, H., Matano, Y., Eds.; Elsevier: New York, 2001;
Chapter 5, pp 371–440; (e) Leonard, N. M.; Wieland, L.
C.; Mohan, R. S. Tetrahedron 2002, 58, 8373.
2
. (a) Challenger, F.; Richards, O. V. J. Chem. Soc. 1934,
405; (b) Barton, D. H. R.; Kitchin, J. P.; Motherwell, W.
7
. In the oxidation of alcohols with Ph BiX (X = OTs,
B. J. Chem. Soc., Chem. Commun. 1978, 1099; (c) Barton,
D. H. R.; Lester, D. J.; Motherwell, W. B.; Papoula, M. T.
B. J. Chem. Soc., Chem. Commun. 1979, 705; (d) Barton,
D. H. R.; Kitchin, J. P.; Lester, D. J.; Motherwell, W. B.;
Papoula, M. T. B. Tetrahedron 1981, 37, 73; (e) Dodonov,
V. A.; Zinov e´ va, T. I.; Osadchaya, N. N. Zh. Obshch.
Khim. 1988, 58, 712; (f) Zinov e´ va, T. I.; Dolganova, N. V.;
Dodonov, V. A.; Prezhbog, I. G. Izv. Akad. Nauk. Ser.
Khim. 1998, 681; (g) Suzuki, H.; Ikegami, T.; Matano, Y.
Tetrahedron Lett. 1994, 35, 8197; (h) Matano, Y.; Nom-
ura, H. J. Am. Chem. Soc. 2001, 123, 6443; (i) Matano, Y.;
Nomura, H.; Suzuki, H.; Shiro, M.; Nakano, H. J. Am.
Chem. Soc. 2001, 123, 10954; (j) Mitsumoto, Y.; Nitta, M.
Bull. Chem. Soc. Jpn. 2003, 76, 1029.
4
OCOCF
3
), triphenylbismuthane and benzene were
formed. See Ref. 4.
. Formation of these products was confirmed by H NMR
and GC.
1
8
9
. Typical procedure: TMG (38 mg, 0.33 mmol) was added
to
a mixture of 1a (213 mg, 0.33 mmol), alcohol
(
0.30 mmol), and CH Cl (10 mL), and the resulting
2
2
mixture was stirred at room temperature. After the alcohol
had been consumed (checked by TLC), the reaction
mixture was concentrated under reduced pressure to
leave an oily residue, which was then subjected on a short
silica gel column (hexane ꢂ hexane/EtOAc or CH
2 2
Cl ).
The carbonyl compounds were easily separated from
triphenylbismuthane and could be isolated in a pure
form.
3
. (a) Matano, Y.; Nomura, H. Angew. Chem., Int. Ed. 2002,
4
1, 3028; (b) Matano, Y.; Hisanaga, T.; Yamada, H.;
Kusakabe, S.; Nomura, H.; Imahori, H. J. Org. Chem.
004, 69, 8676.
1
0. At present, we assume that the ground state of 1a/TMG/
alcohol is destabilized compared to the alkoxybismuth(V)
intermediate in a nonpolar solvent such as toluene. The
solvent effect will be investigated systematically in the
future work.
2
4
. Barton, D. H. R.; Finet, J.-P.; Motherwell, W. B.; Pichon,
C. J. Chem. Soc., Perkin Trans. 1 1987, 251. In the
0
0
00
00
presence of N-butyl-N ,N ,N ,N -tetramethylguanidine,
these alcohols were oxidized to the corresponding car-
bonyl compounds in 78–92% yields after 7.5–12 h.
. (a) Matano, Y.; Begum, S. A.; Miyamatsu, T.; Suzuki, H.
Organometallics 1998, 17, 4332; (b) Matano, Y.; Begum, S.
A.; Miyamatsu, T.; Suzuki, H. Organometallics 1999, 18,
1
1
1. The formation of 2-mesityldodecanal was suggested by the
1
H NMR spectrum of the reaction mixture. This byprod-
uct was presumably formed by C-arylation of the initial
product, dodecanal, with 1a/TMG.
5
2. For the primary selective oxidation methods, see: (a)
Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetra-
hedron Lett. 1981, 22, 1605; (b) Semmelhack, M. F.; Chou,
C. S.; Cortes, D. A. J. Am. Chem. Soc. 1983, 105, 4492; (c)
Inokuchi, T.; Matsumoto, S.; Nishiyama, T.; Torii, S. J.
Org. Chem. 1990, 55, 462; (d) Einhorn, J.; Einhorn, C.;
Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452;
2 2
5668. Typical procedure: To a CH Cl solution (25 mL)
containing triphenylbismuth difluoride (2.39 g, 5.00 mmol)
and mesitylboronic acid (0.90 g, 5.5 mmol) was added
BF ÆOEt (0.78 mL, 6.0 mmol) at 0 °C, and the mixture
3
2
was stirred for 2 h at room temperature. An aqueous
solution of NaBF
the resulting two-phase solution was vigorously stirred for
0 min. The aqueous phase was separated and extracted
with CH Cl . The combined organic extracts were dried
over MgSO , passed through a short silica gel column, and
evaporated under reduced pressure to leave a solid residue,
which was reprecipitated from CH Cl –Et O to afford 1a
3.17 g, 98%) as a colorless solid. H NMR (CDCl ): d 2.33
4
(17 g, 150 mmol) was then added, and
(
2
e) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett.
001, 3, 3041; (f) Dijksman, A.; Marino-Gonz a´ lez, A.;
2
Mairata i Payeras, A.; Arends, I. W. C. E.; Sheldon, R. A.
J. Am. Chem. Soc. 2001, 123, 6826; (g) Jiang, N.;
Ragauskas, A. J. Org. Lett. 2005, 7, 3689; (h) Gilhespy,
M.; Lok, M.; Baucherel, X. Chem. Commun. 2005, 1085,
and references cited therein.
2
2
4
2
2
2
1
(
3