Organic Letters
Letter
Al-Zahrani, S. M.; Fierro, J. L. G.; Alonso, J. A. Angew. Chem., Int. Ed.
Gerth, K.; Bo
Zeilinger, C.; Kirschning, A.; Mu
51, 1256.
(14) Masters, K.-S.; Bras
̈
hlendorf, B.; Ho
̈
fle, G.; Reichenbach, H.; Wegner, J.;
2
(
5
5
011, 50, 6557.
2) (a) Meciarova, M.; Toma, S.; Heribanova,
6, 8561. (b) Strazzolini, P.; Runcio, A. Eur. J. Org. Chem. 2003, 2003,
26. (c) Silvestre, S. M.; Salvador, J. A. R. Tetrahedron 2007, 63, 2439.
̈
ller, R. Angew. Chem., Int. Ed. 2012,
̌
́
A. Tetrahedron 2000,
̈
e, S. Chem. Rev. 2012, 112, 3717.
(15) For recent examples, see: (a) Napoly, F.; Kieffer, R.; Jean-
Gerard, L.; Goux-Henry, C.; Draye, M.; Andrioletti, B. Tetrahedron
Lett. 2015, 56, 2517. (b) Urgoitia, G.; SanMartin, R.; Herrero, M. T.;
Dominguez, E. Chem. Commun. 2015, 51, 4799. (c) Li, J.-K.; Huang,
X.-Q.; Yang, S.; Ma, H.-W.; Chi, Y.-N.; Hu, C.-W. Inorg. Chem. 2015,
54, 1454. (d) Nguyen, T.-A. D.; Wright, A. M.; Page, J. S.; Wu, G.;
Hayton, T. W. Inorg. Chem. 2014, 53, 11377. (e) Chen, Y.; Huang, X.;
Feng, X.; Li, J.; Huang, Y.; Zhao, J.; Guo, Y.; Dong, X.; Han, R.; Qi, P.;
Han, Y.; Li, H.; Hu, C.; Wang, B. Chem. Commun. 2014, 50, 8374.
(f) Mahyari, M.; Laeini, M. S.; Shaabani, A. Chem. Commun. 2014, 50,
7855. (g) Shen, D.; Miao, C.; Wang, S.; Xia, C.; Sun, W. Org. Lett.
2014, 16, 1108.
(
d) Dohi, T.; Takenaga, N.; Goto, A.; Fujioka, H.; Kita, Y. J. Org.
Chem. 2008, 73, 7365. (e) Richter, H.; Mancheno, O. G. Eur. J. Org.
Chem. 2010, 23, 4460. (f) Song, A. R.; Yu, J.; Zhang, C. Synthesis 2012,
4, 2903. (g) Nammalwar, B.; Fortenberry, C.; Bunce, R. A.;
Lageshetty, S. K.; Ausman, K. D. Tetrahedron Lett. 2013, 54, 2010.
h) Zhang, C.; Srivastava, P.; Guardiola, K. E.; Lewis, J. C. Tetrahedron
014, 70, 4245.
3) (a) Khenkin, A. M.; Neumann, R. J. Am. Chem. Soc. 2002, 124,
198. (b) Gonsalvi, L.; Arends, I. W. C. E.; Moilanen, P.; Sheldon, R.
̃
4
(
2
(
4
A. Adv. Synth. Catal. 2003, 345, 1321. (c) Catino, A. J.; Nichols, J. M.;
Choi, H.; Gottipamula, S.; Doyle, M. P. Org. Lett. 2005, 7, 5167.
(
d) Nakanishi, M.; Bolm, C. Adv. Synth. Catal. 2007, 349, 861. (e) Li,
(16) Catalyst I was recycled by simple evaporation of CH CN, and
then the reaction product was distributed in Et O and the catalyst into
3
H.; Li, Z.; Shi, Z. Tetrahedron 2009, 65, 1856. (f) Kumar, R. A.;
Maheswari, C. U.; Ghantasala, S.; Jyothi, C.; Reddy, K. R. Adv. Synth.
Catal. 2011, 353, 401. (g) Ang, W. J.; Lam, Y. L. Org. Biomol. Chem.
2
(
17) Sudo, A.; Endo, T.; Suzuki, A. Low Shrinkage Epoxy-Cationic
Curable Compositions, WO Patent 2007135094, November 29, 2007.
18) Kobayashi, S.; Kihara, M.; Hashimoto, T.; Kitamura, K.
Yakugaku Zasshi 1975, 95, 1449.
19) Moore, J. H.; Davis, N. D.; Diener, U. L. Appl. Microbiol. 1972,
3, 1067.
20) (a) Sun, H. H.; Ho, C. L.; Ding, F. Q.; Soehano, I.; Liu, X. W.;
Liang, Z. X. J. Am. Chem. Soc. 2012, 134, 11924. (b) Kerti, G.; Kurtan
T.; Illyes, T. Z.; Kover, K. E.; Solyom, S.; Pescitelli, G.; Fujioka, N.;
2
(
1
015, 13, 1048.
4) (a) Sen, A.; Lin, M.; Kao, L. C.; Hutson, A. C. J. Am. Chem. Soc.
992, 114, 6385. (b) Fazlur-Rahman, A. K.; Tsai, J. C.; Nicholas, K. M.
(
J. Chem. Soc., Chem. Commun. 1992, 1334. (c) Reetz, M. T.; Tollner,
K. Tetrahedron Lett. 1995, 36, 9461. (d) Shi, M. J. Chem. Res., Synop.
(
2
(
1
998, 9, 592. (e) Kawabata, H.; Hayashi, M. Tetrahedron Lett. 2004,
4
5, 5457.
́
,
(
5) Gonzalez-de-Castro, A.; Robertson, C. M.; Xiao, J.-L. J. Am.
́
̈
́
́
Chem. Soc. 2014, 136, 8350.
Berova, N.; Antus, S. Eur. J. Org. Chem. 2007, 2007, 296. (c) Islam, M.
S.; Ishigami, K.; Watanabe, H. Tetrahedron 2007, 63, 1074.
(
6) Ciriminna, R.; Pagliaro, M. Org. Process Res. Dev. 2010, 14, 245.
(
7) For recent reviews of TEMPO-catalyzed alcohol oxidations, see:
(
(
a) Tebben, L.; Studer, A. Angew. Chem., Int. Ed. 2011, 50, 5034.
b) Wertz, S.; Studer, A. Green Chem. 2013, 15, 3116. (c) Ryland, B.
L.; Stahl, S. S. Angew. Chem., Int. Ed. 2014, 53, 8824. (d) Cao, Q.;
Dornan, L. M.; Rogan, L.; Hughes, L. N.; Muldoon, M. J. Chem.
Commun. 2014, 50, 4524.
(
8) New TEMPO analogues: (a) Shibuya, M.; Tomizawa, M.; Suzuki,
I.; Iwabuchi, Y. J. Am. Chem. Soc. 2006, 128, 8412. (b) Graetz, B.;
Rychnovsky, S.; Leu, W.-H.; Farmer, P.; Lin, R. Tetrahedron:
Asymmetry 2005, 16, 3584. (c) Amar, M.; Bar, S.; Iron, M. A.;
Toledo, H.; Tumanskii, B.; Shimon, L. J. W.; Botoshansky, M.;
Fridman, N.; Szpilman, A. M. Nat. Commun. 2015, 6, 6070.
(
9) Catalytic oxidation processes: (a) Alcohols to carboxylic acids:
Shibuya, M.; Sato, T.; Tomizawa, M.; Iwabuchi, Y. Chem. Commun.
009, 1739. (b) 1,2-Diols to (di)carboxylic acids: Shibuya, M.;
2
Shibuta, T.; Fukuda, H.; Iwabuchi, Y. Org. Lett. 2012, 14, 5006. (c)
Primary amines to nitriles: Kim, J.; Stahl, S. S. ACS Catal. 2013, 3,
1
652. (d) 1,2-Diols to α-hydroxy acids: Furukawa, K.; Shibuya, M.;
Yamamoto, Y. Org. Lett. 2015, 17, 2282. (e) Arylation of isochromans:
Muramatsu, W.; Nakano, K. Org. Lett. 2015, 17, 1549. Stoichiometric
oxidations: (f) Benzylic ethers to aldehydes: Pradhan, P. P.; Bobbitt,
J. M.; Bailey, W. F. J. Org. Chem. 2009, 74, 9524. (g) Aliphatic C−H
bonds with oximes and hydrazones: Zhu, X.; Wang, Y.-F.; Zhang, F.-
L.; Chiba, S. Org. Lett. 2013, 15, 3214.
(
10) For recent examples, see: (a) Wang, S.-N.; Li, X.-M.; Liu, H.-W.;
Xu, L.; Zhuang, J.-C.; Li, J.; Li, H.; Wang, W. J. Am. Chem. Soc. 2015,
37, 2303. (b) Chen, J.; Li, J.; Wang, J.; Li, H.; Wang, W.; Guo, Y.-W.
1
Org. Lett. 2015, 17, 2214. (c) Song, A.-G.; Zhang, X.-S.; Song, X.-X.;
Chen, X.-B.; Yu, C.-G.; Huang, H.; Li, H.; Wang, W. Angew. Chem., Int.
Ed. 2014, 53, 4940. (d) Zhang, X.-S.; Song, X.-X.; Li, H.; Zhang, S.-L.;
Chen, X.-B.; Yu, X.-H.; Wang, W. Angew. Chem., Int. Ed. 2012, 51,
7
282. (e) Song, X.-X.; Song, A.-G.; Zhang, F.; Li, H.-X.; Wang, W. Nat.
Commun. 2011, 2, 524.
(
(
12) (a) Liu, R.-H.; Liang, X.-M.; Dong, C.-Y.; Hu, X.-Q. J. Am.
Chem. Soc. 2004, 126, 4112. (b) Wang, X.-L.; Liu, R.-H.; Jin, Y.; Liang,
X.-M. Chem. - Eur. J. 2008, 14, 2679.
(
13) (a) Mc Inerney, B. V.; Taylor, W. C. Stud. Nat. Prod. Chem.
1
995, 15, 381. (b) Barbier, J.; Jansen, R.; Irschik, H.; Benson, S.;
D
Org. Lett. XXXX, XXX, XXX−XXX