Please do not adjust margins
Organic & Biomolecular Chemistry
Page 4 of 5
ARTICLE
Journal Name
standard condition
OH
O
6
7
A. De, J. Sci. Ind. Res., 1982, 41, 484-494.
D. B. Dess and J. C. Martin, J. Org. CDhOemI: 1.,0.11093V89i3e/wC, 5A4Or8tiBc,l0e41O18n53li45nJe-
4156.
radical scavenger(0.6equiv)
O2N
O2N
1a
TEMPO, 2a, 2%
BHT,2a, trace
8
9
M. Uyanik and K. Ishihara, Chem. Commun., 2009, 2086-2099.
A. J. Mancuso, S. L. Huang and D. Swern, J. Org. Chem., 1978,
43, 2480-2482.
N
O
O
OH
OH
10 A. J. Mancuso, D. S. Brownfain and D. Swern, J. Org. Chem.,
1979, 44, 4148-4151.
O2N
Intermediate A
O2N
Intermediate B
11 G. Piancatelli, A. Scettri and M. Dauria, Synthesis, 1982, 245-
258.
Scheme 3 Control Experiments under Standard Conditions
12 M. Frigerio and M. Santagostino, Tetrahedron Lett., 1994, 35,
8019-8022.
13 S. Tanaka, Y. Kon, T. Nakashima and K. Sato, RSC Adv., 2014,
4, 37674.
To validate this mechanism, two control experiments were
performed.
When 0.6 equivalents of 2, 2, 6, 6-tetramethylpiperidinooxy
were added to the reaction mixture, a significant decrease of
the yield was observed (from 95% to 2%), which revealed that
this reaction involved a radical process.42, 43 Similarly, adding 2,
6-ditertbutyl-4-methylphenol to the reaction mixture failed to
afford the corresponding aldehyde. In addition, the
intermediate A and B were detected with the help of high
resolution mass spectrometry when TEMPO and BHT were
involved respectively, which approved the existence of
intermediate 2 and supported the mechanism strongly.
14 E. Nikbakht, B. Yadollahi and M. R. Farsani, Inorg. Chem.
Commun., 2015, 55, 135-138.
15 M. Szávuly, S. D. Szilvási, R. Csonka, D. Klesitz, G. Speier, M.
Giorgi and J. Kaizer, J. Mole. Catal. A-Chem., 2014, 393, 317-
324.
16 M. R. Farsani, F. Jalilian, B. Yadollahi and H. A. Rudbari,
Polyhedron, 2014, 76, 102-107.
17 Z. Nadealian, V. Mirkhani, B. Yadollahi, M. Moghadam, S.
Tangestaninejad and I. Mohammadpoor-Baltork, J. Coord.
Chem., 2013, 66, 1264-1275.
18 B. Karimi, F. B. Rostami, M. Khorasani, D. Elhamifar and H.
Vali, Tetrahedron, 2014, 70, 6114-6119.
19 D. Sloboda-Rozner, P. L. Alsters and R. Neumann, J. Am.
Chem. Soc., 2003, 125, 5280-5281.
20 K. Sato, M. Aoki, J. Takagi and R. Noyori, J. Am. Chem. Soc.,
1997, 119, 12386-12387.
21 R. Noyori, M. Aoki and K. Sato, Chem. Commun., 2003, 1977.
22 Y. Zhang, Q. Zhou, W. Ma and J. Zhao, Catal. Commun., 2014,
45, 114-117.
23 V. Pandarus, R. Ciriminna, F. Beland, G. Gingras, M. Drobot,
O. Jina and M. Pagliaro, Tetrahedron Lett., 2013, 54, 1129-
1132.
24 M. Z. Zhao, J. Li, E. Mano, Z. G. Song, D. M. Tschaen, E. J. J.
Grabowski and P. J. Reider, J. Org. Chem., 1999, 64, 2564-
2566.
25 Z. Zheng, J. Wang, M. Zhang, L. Xu and J. Ji, Chemcatchem,
2013, 5, 307-312.
Conclusions
In conclusion, a green and economic aerobic oxidation of
benzylic alcohols, hetero aryl alcohols and allyl alcohol were
developed, affording the corresponding carbonyl compounds
with moderate to excellent yields and functional group
tolerance.
A
variety of aldehydes and ketones were
synthetized using this oxidation system. In addition, a radical
process was assumed and approved. Further investigation into
the detailed mechanism was ongoing in our laboratory.
26 A. B. Leduc and T. F. Jamison, Org. Process Res. Dev., 2012,
16, 1082-1089.
Acknowledgements
27 Y. Zhang, S. C. Born and K. F. Jensen, Org. Process Res. Dev.,
2014, 18, 1476-1481.
The research has been supported by National Key Basic
Research Program of China (973 Program) 2012CB725204;
the National High Technology Research and Development
Program of China (863 Program) 2014AA022101; the
National Natural Science Foundation of China (Grant
No.U1463201, 81302632 and 21402240); Jiangsu Province
28 T. Mallat and A. Baiker, Chem. Rev., 2004, 104, 3037-3058.
29 D. I. Enache, J. K. Edwards, P. Landon, B. Solsona-Espriu, A. F.
Carley, A. A. Herzing, M. Watanabe, C. J. Kiely, D. W. Knight
and G. J. Hutchings, Science, 2006, 311, 362-365.
30 S. E. Davis, M. S. Ide and R. J. Davis, Green Chem., 2013, 15,
17-45.
Natural
Science
Fund (Grant
No. 13KJA150002,
31 S. M. Alia, K. Duong, T. Liu, K. Jensen and Y. Yan,
ChemSusChem, 2014, 7, 1739-1744.
32 J. M. Hoover and S. S. Stahl, J. Am. Chem. Soc., 2011, 133,
16901-16910.
BK20130913 and BY201400503); the National Science and
Technology Major Projects for "Major New Drugs
Innovation and Development" (2013ZX09103001-004).
33 I. A. Ansari and R. Gree, Org. Lett., 2002, 4, 1507-1509.
34 M. Zhang, C. Chen, W. Ma and J. Zhao, Angew. Chem. Int. Ed.,
2008, 47, 9730-9733.
35 B. Xu, J.-P. Lumb and B. A. Arndtsen, Angew. Chem. Int. Ed.,
2015, 54, 4208-4211.
36 L. Wang, J. Li, H. Yang, Y. Lv and S. Gao, J. Org. Chem., 2012,
77, 790-794.
37 Z. Shen, J. Dai, J. Xiong, X. He, W. Mo, B. Hu, N. Sun and X. Hu,
Adv. Synth. Catal., 2011, 353, 3031-3038.
38 K. Walsh, H. F. Sneddon and C. J. Moody, Org. Lett., 2014, 16,
5224-5227.
39 C-K. Liu, Z. Fang, Z. Yang, Q-W. Li, S-Y. Guo, K. Zhang, P-K.
Ouyang and K. Guo, Tetrahedron Lett., 2015, 56, 5973.
Notes and references
1
J. W. Ladbury and C. F. Cullis, Chem. Rev., 1958, 58, 403-438.
H. Du, P. K. Lo, Z. Hu, H. Liang, K. C. Lau, Y. N. Wang, W. W.
Lam and T. C. Lau, Chem. Commun., 2011, 47, 7143-7145.
A. Kamimura, Y. Nozaki, S. Ishikawa, R. Inoue and M.
Nakayama, Tetrahedron Lett., 2011, 52, 538-540.
C. S. Kovash, Jr., E. Pavlacky, S. Selvakumar, M. P. Sibi and D.
C. Webster, ChemSusChem, 2014, 7, 2289-2294.
E. Corey and J. W. Suggs, Tetrahedron Lett., 1975, 16, 2647-
2650.
2
3
4
5
4 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins