3
Wang, X. Li, J.-W. Guo, B. Wang, Tetrahedron Lett. 2014, 55,
058.
It is noteworthy to mention that a gram-scale practical
5
reaction was successfully carried out to give the bromination
product, as exemplified by the bromination of 1-decene to the
dibromide in 74% isolated yield (Scheme 2).
Bu4NBr 200 mol%
TFA
H2O2
300 mol%
300 mol%
Br
Br
7
7
H2O, Ar, 25 C, 5 h
1
.05 g
1, 1.67 g
4% (isolated yield)
7
Scheme 2 Gram-scale bromination reaction of 1-decene in water
by using Bu4NBr/TFA/H2O2 system.
In conclusion, a combination of tetrabutylammonium
bromide as a bromide source, trifluoroacetic acid as an acid,
and hydrogen peroxide as an oxidant has been demonstrated
to induce metal-free oxidative bromination reactions in
aqueous media under mild conditions. This oxidative
bromination system could be applied to the oxidative
bromination of alkenes, alkynes, arenes, and 3,4-
dihydronaphthalen-1(2H)-one.
A
gram-scale brominaton
reaction was also performed successfully. Future work will
concentrate on synthetic versatility and application of this
practical method to other reactions.
This work was supported partly by the ACT-C program
of Japan Science and Technology Agency (JST). Thanks are
due to the Analytical Center, Graduate School of Engineering,
Osaka University.
Supporting Information is available on http://dx.doi.org/.
References and Notes
1
a) V. Conte, F. Di Furia, S. Moro, Tetrahedron Lett. 1994, 35, 7429.
b) R. K. Dieter, L. E. Nice, S. E. Velu, Tetrahedron Lett. 1996, 37,
2
377. c) V. Nair, S. B. Panicker, A. Augstine, T. G. George, S.
Thomas, M. Vairamani, Tetrahedron 2001, 57, 7417. d) K. G.
Dewkar, V. S. Narina, A. Sudalai, Org. Lett. 2003, 5, 4501. e) H. A.
Muathen Synth. Commun. 2004, 34, 3545. f) C. Ye, M. J. Shreeve,
J. Org. Chem. 2004, 69, 8561. g) G. Zhang, R. Liu, Q. Xu, L. Ma,
X. Liang, Adv. Synth. Catal. 2006, 348, 862. h) T. Moriuchi, M.
Yamaguchi, K. Kikushima, T. Hirao, Tetrahedron Lett. 2007, 48,
2
667. i) M. Eissen, D. Lenoir, Chem. Eur. J. 2008, 14, 9830. j) L.
Yang, Z. Lu, S. S. Stahl, Chem. Commun. 2009, 6460. k) A.
Podgoršek, M. Zupan, J. Iskra, Angew. Chem. Int. Ed. 2009, 48,
8
424. l) G.-W. Wang, J. Gao, Green Chem. 2012, 14, 1125. m) R.
Prebil, K. K. Laali, S. Stavber, Org. Lett. 2013, 15, 2108. n) H.
Kajita, A. Togni, ChemistrySelect, 2017, 2, 1117. o) K. Moriyama,
T. Hamada, Y. Nakamura, H. Togo, Chem. Commun. 2017, 53,
6
565.
2
a) K. Kikushima, T. Moriuchi, T. Hirao, Chem. Asian J. 2009, 4,
1
2
213. b) K. Kikushima, T. Moriuchi, T. Hirao, Tetrahedron Lett.
010, 51, 340. c) K. Kikushima, T. Moriuchi, T. Hirao,
Tetrahedron 2010, 66, 6906.
3
4
A. Butler, J. V. Walker, Chem. Rev. 1993, 93, 1937.
T. Moriuchi, Y. Fukui, S. Kato, T. Kajikawa, T. Hirao, J. Inorg.
Biochem. 2015, 147, 177.
5
a) G. Majetich, R. Hicks, S. Reister, J. Org. Chem. 1997, 62, 4321.
b) C. Liu, R. Dai, G. Yao, Y. Deng, J. Chem. Res. 2014, 38, 593. c)
S. Song, X. Sun, X. Li, Y. Yuan, N. Jiao, Org. Lett. 2015, 17, 2886.
d) M. Karki, J. Magolan, J. Org. Chem. 2015, 80, 3701. e) S. Song,
X. Li, X. Sun, Y. Yuan, N. Jiao, Green Chem. 2015, 17, 3285.
a) T.-L. Ho, B. G. B. Gupta, G. A. Olah, Synthesis 1977, 676. b) J.
Dakka, Y. Sasson, J. Chem. Soc., Chem. Commun. 1987, 1421. c)
M. Ghaffarzadeh, M. Bolourtchian, K. Tabar-Heydar, I. Daryaei, F.
Mohsenzadeh, J. Chem. Sci. 2009, 121, 177. d) T. Xu, W. Zhou, J.
6