Organic Letters
Letter
Rhode, O.; Takai, T.; Mukaiyama, T. Chem. Lett. 1991, 20, 5.
(23) Minisci, F.; Gambarotti, C.; Pierini, M.; Porta, O.; Punta, C.;
Recupero, F.; Lucarini, M.; Mugnaini, V. Tetrahedron Lett. 2006, 47,
1421.
(
d) Vanoye, L.; Pablos, M.; Smith, N.; de Bellefon, C.; Favre-
Reguillon, A. RSC Adv. 2014, 4, 57159. (e) Yu, H.; Ru, S.; Dai, G.;
Zhai, Y.; Lin, H.; Han, S.; Wei, Y. Angew. Chem., Int. Ed. 2017, 56,
3
8
867. (f) Jiang, X.; Zhang, J.; Ma, S. J. Am. Chem. Soc. 2016, 138,
344. (g) Jiang, X.; Zhai, Y.; Chen, J.; Han, Y.; Yang, Z.; Ma, S. Chin.
J. Chem. 2018, 36, 15.
(
(
5) Dai, P. F.; Qu, J. P.; Kang, Y. B. Org. Lett. 2019, 21, 1393.
6) (a) Lehtinen, C.; Nevalainen, V.; Brunow, G. Tetrahedron 2001,
5
7, 4741. (b) Denisov, E. T.; Afanas’ev, I. B. Oxidation and
Antioxidants in Organic Chemistry and Biology; Taylor & Francis:
Boca Raton, FL, 2005.
(
(
7) Renz, M.; Meunier, B. Eur. J. Org. Chem. 1999, 1999, 737.
8) Lehtinen, C.; Nevalainen, V.; Brunow, G. Tetrahedron 2000, 56,
9
375.
9) (a) Krow, G. R. The Baeyer−Villiger Oxidation of Ketones and
Aldehydes. Organic Reactions; John Wiley & Sons: 1993; Vol. 43, p
51. (b) Horn, A.; Kazmaier, U. Eur. J. Org. Chem. 2018, 2018, 2531.
c) Richter, S. C.; Oestreich, M. Chem. - Eur. J. 2019, 25, 8508.
10) da Silva, E. T.; Camara, C. A.; Antunes, O. A. C.; Barreiro, E. J.;
Fraga, C. A. M. Synth. Commun. 2008, 38, 784.
11) Aerobically generated peracids have been utilized for the
(
2
(
(
̂
(
epoxidation of olefins (i.e., Mukaiyama epoxidation); see: (a) Yamada,
T.; Takai, T.; Rhode, O.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1991,
6
4, 2109. (b) Vanoye, L.; Wang, J.; Pablos, M.; de Bellefon, C.; Favre-
Reguillon, A. Catal. Sci. Technol. 2016, 6, 4724. For the BV oxidation
of ketones, see: (c) Kaneda, K.; Ueno, S.; Imanaka, T.; Shimotsuma,
E.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1994, 59, 2915. (d) Nabae,
Y.; Rokubuichi, H.; Mikuni, M.; Kuang, Y.; Hayakawa, T.; Kakimoto,
M.-a. ACS Catal. 2013, 3, 230. (e) Wang, L.; Wang, Y.; Du, R.; Dao,
R.; Yuan, H.; Liang, C.; Yao, J.; Li, H. ChemCatChem 2018, 10, 4947.
For the hydroxylation of 2-arylpyridines, see: (f) Das, P.; Saha, D.;
Saha, D.; Guin, J. ACS Catal. 2016, 6, 6050. For the hydroacylation
of olefins, see: (g) Shapiro, N.; Kramer, M.; Goldberg, I.; Vigalok, A.
Green Chem. 2010, 12, 582. (h) Alvarez, L. X.; Kudrik, E. V.; Sorokin,
A. B. Chem. - Eur. J. 2011, 17, 9298. For the oxidation of iodobenzene
to form hypervalent iodine intermediates, see: (i) Maity, A.; Hyun, S.
M.; Powers, D. C. Nat. Chem. 2018, 10, 200. (j) Chauhan, J.; Ravva,
(
(
(
13) Nedelec, J. Y.; Sorba, J.; Lefort, D. Synthesis 1976, 1976, 821.
14) Violet, L.; Mifleur, A.; Vanoye, L.; Nguyen, D. H.; Favre-
Reg
Eng. 2019, 4, 909.
15) Di Furia, F.; Prato, M.; Quintily, U.; Salvagno, S.; Scorrano, G.
Analyst 1984, 109, 985.
16) (a) Silbert, L. S.; Siegel, E.; Swern, D. Org. Synth. 1964, 44, 81.
b) Harman, D. G.; Ramachandran, A.; Gracanin, M.; Blanksby, S. J. J.
Org. Chem. 2006, 71, 7996.
17) Hussain, H.; Al-Harrasi, A.; Green, I. R.; Ahmed, I.; Abbas, G.;
Rehman, N. U. RSC Adv. 2014, 4, 12882.
18) (a) Vanoye, L.; Wang, J.; Pablos, M.; Philippe, R.; Bellefon, C.
d.; Favre-Reguillon, A. Org. Process Res. Dev. 2016, 20, 90. (b) Raju,
R.; Prasad, K. Tetrahedron 2012, 68, 1341.
19) Vanoye, L.; Favre-Reguillon, A.; Aloui, A.; Philippe, R.; de
Bellefon, C. RSC Adv. 2013, 3, 18931.
20) Evans, D. F.; Upton, M. W. J. Chem. Soc., Dalton Trans. 1985,
151.
21) (a) Davis, R.; Lovelace, T. C.; Martinez, N. J.; Millar, A. Catal.
́
uillon, A.; Philippe, R.; Gauvin, R. M.; Fongarland, P. React. Chem.
(
(
(
(
(
́
(
(
1
(
Lett. 1995, 31, 307. (b) Hendriks, C. F.; Vanbeek, H. C. A.; Heertjes,
P. M. Ind. Eng. Chem. Prod. Res. Dev. 1979, 18, 38. (c) Popov, E.;
Eloranta, J.; Hietapelto, V.; Vuorenpalo, V. M.; Aksela, R.; Jakara, J.
Holzforschung 2005, 59, 507. (d) Zhao, X.; Cheng, K.; Hao, J.; Liu, D.
J. Mol. Catal. A: Chem. 2008, 284, 58.
(
22) (a) Sanchez, J.; Myers, T. N. Organic Peroxides. In Kirk-
Othmer Encyclopedia of Chemical Technology, 4th ed.; John Wiley &
Sons: New York, 1993; Vol. 18, p 101. (b) Fossey, J.; Lefort, D.;
Sorba, J. Top. Curr. Chem. 1993, 164, 99.
E
Org. Lett. XXXX, XXX, XXX−XXX