RSC Advances
COMMUNICATION
4RA0813
DOI: 10.1039Jo/Curnal Na3Ame
Scheme 2. Proposed reaction mechanism
Acknowledgements
3
For selected articles of alcohol oxidation using oxoammonium
salts, see: ( ) Z. Ma, J. M. Bobbitt, J. Org. Chem. 1991, 56
6110ꢀ6114; ( ) J. M. Bobbitt, J. Org. Chem. 1998, 63, 9367ꢀ
9374; ( ) N. Merbouh, J. M. Bobbitt, C. Brückner, J. Org.
Chem. 2004, 69, 5116ꢀ5119; ( ) W. F. Bailey, J. M. Bobbitt,
J. Org. Chem. 2007, 72, 4504ꢀ4509; ( ) C. B. Kelly, M. A.
Mercadante, T. A. Hamlin, M. H. Fletcher, N. E. Leadbeater,
J. Org. Chem. 2012, 77, 8131ꢀ8141; ( ) J. C. Qiu, P. P.
Pradhan, N. B. Blanck, J. M. Bobbitt, W. F. Bailey, Org. Lett.
2012, 14, 350ꢀ353; ( ) C. B. Kelly, M. A. Mercadante, R. J.
This study was supported by the Korea Research Foundation (No.
009ꢀ0094046 and 2013008819) and the Korea CCS R&D Center
KCRC) grant funded by the Korea Government (Ministry of Education,
a
,
2
b
(
c
Science and Technology) (No. 2014M1A8A1049294).
d
e
Notes and references
a
Department of Energy Systems Research, Ajou University, Suwon 443ꢀ
f
7
49, Korea, Eꢀmail:hyjang2@ajou.ac.kr; Fax: +82312191615; Tel: +82
1 219 2555
3
b
g
Korea Carbon Capture & Sequestration R&D Center, Deajeon 305ꢀ343,
Korea.
Wiles, N. E. Leadbeater, Org. Lett. 2013, 15, 2222ꢀ2225.
4
5
For NHCꢀcatalyzed oxidation of aldehydes using TEMPO,
†
Electronic Supplementary Information (ESI) available: detailed
see: (
Chem. Int. Ed. 2008, 47, 8727ꢀ8730; (
N. Lim, Y.ꢀW. Kang, H.ꢀY. Jang, Eur. J. Org. Chem. 2013,
881ꢀ7885; ( ) M. Ji, S. Lim, H.ꢀY. Jang, RSC Advances
2014, , 28225ꢀ28228.
For selected articles of singleꢀelectronꢀtransfer by organic
reagents, see: ( ) J. A. Murphy, T. A. Jhan, S.ꢀz. Zhou, D. W.
Thomson, M. Mahesh, Angew. Chem. Int. Ed. 2005, 44, 1356ꢀ
1360; ( ) F. Schoenebeck, J. A. Murphy, S.ꢀz. Zhou, Y.
Uenoyama, Y. Miclo, T. Tuttle, J. Am. Chem. Soc. 2007, 129
13368ꢀ13369; ( ) G. P. McGlacken, T. A. Khan, Angew.
a
) J. Guin, S. De Sarkar, S. Grimme, A. Studer, Angew.
experimental and spectral analysis for new compounds. See
DOI: 10.1039/c000000x/
b
) M. Ji, X. Wang, Y.
7
c
,
1
For review articles using nitroxide radicals and oxoammonium
salts for oxidation, see: ( ) J. M. Bobbitt, M .C. L. Flores,
Heterocycles 1988, 27, 509ꢀ533; ( ) A. E. J. de Nooy, A. C.
Besemer, H. van Bekkum, Synthesis 1996, 1153ꢀ1174; ( ) R.
A. Sheldon, I. W. C. E. Arends, G.ꢀJ. T. Brink, A. Dijksman,
Acc. Chem. Res. 2002, 35, 774ꢀ781; ( ) N. Merbouh, J. M.
Bobbitt, C. Brückner, Org. Prep. Proced. Int. 2004, 36, 1ꢀ31;
) R. A. Sheldon, I. W. C. E. Arends, Adv. Synth. Catal.
004, 346, 1051ꢀ1071; ( ) T. Vogler, A. Studer, Synthesis
008, 1979ꢀ1993; ( ) L. Tebben, A. Studer, Angew. Chem. Int.
4
a
b
a
c
b
d
,
c
(
e
Chem. Int. Ed. 2008, 47, 1819ꢀ1823; (d) G. J. Rowlands,
2
2
f
Tetrahedron 2009, 65, 8603ꢀ8655.
g
6
For selected articles of NHCꢀcatalyzed oxidation, see: (
E. Maki, K. A. Scheidt, Org. Lett. 2008, 10, 4331ꢀ4334; (
Noonan, L. Baragwanath, S. J. Cannon, Tetrahedron Lett.
2008, 49, 4003ꢀ4006; ( ) B. E. Maki, A. Chan, E. M. Phillips,
K. A. Scheidt, Tetrahedron 2009, 65, 3102ꢀ3109; ( ) S. De
Sarkar, S. Grimme, A. Studer, J. Am. Chem. Soc. 2010, 132
a
) B.
Ed. 2011, 50, 5034ꢀ5068.
b
) C.
2
For selected articles of nitroxideꢀcatalyzed alcohol oxidation,
see: (
004, 126, 4112ꢀ4113; (
M. Benaglia, G. Dell Anna, Org. Lett. 2004,
I. Herrerías, T. Y. Zhang, C.ꢀJ. Li, Tetrahedron Lett. 2006, 47
3ꢀ17; ( ) Y. Xie, W. Mo, D. Xu, Z. Shen, N. Sun, B. Hu, X.
Hu, J. Org. Chem. 2007, 72, 4288ꢀ4291; ( ) X. Wang, R. Liu,
Y. Jin, X. Liang, Chem. Eur. J. 2008, 14, 2679ꢀ2685; ( ) C.ꢀX.
Miao, L.ꢀN. He, J.ꢀQ. Wang, J.ꢀL. Wang, Adv. Synth. Catal.
009, 351, 2209ꢀ2216; ( ) C.ꢀX. Miao, L.ꢀN. He, J.ꢀL. Wang,
F. Wu, J. Org. Chem. 2010, 75, 257ꢀ260; ( ) M. Hayashi, M.
Shibuya, Y. Iwabuchi, J. Org. Chem. 2012, 77, 3005ꢀ3009.
a
) R. Liu, X. Liang, C. Dong, X. Hu, J. Am. Chem. Soc.
) G. Pozzi, M. Cavazzini, S. Quici,
, 441ꢀ443; ( ) C.
c
2
b
d
′
6
c
,
,
,
,
1190ꢀ1191; (
1992ꢀ1995; (
4552ꢀ4555; (
Liu, J. Org. Chem. 2011, 76, 3016ꢀ3023; (
W. Bode, Org. Lett. 2011, 13, 2422ꢀ2425; (
e
) S. De Sarkar, A. Studer, Org. Lett. 2010, 12
1
d
f) C. A. Rose, K. Zeitler, Org. Lett. 2010, 12
e
g) B. Maji, S. Vedachalan, X. Ge, S. Cai, X.ꢀW.
f
h
) P.ꢀC. Chiang, J.
i
) E. E. Finney, K.
2
g
A. Ogawa, A. J. Boydston, J. Am. Chem. Soc. 2012, 134
,
h
12374ꢀ12377; ( ) P. Arde, B. T. Ramanjaneyulu, V. Reddy, A.
j
Saxena, R. V. Anand, Org. Biomol. Chem. 2012, 10, 848ꢀ851;
4
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