1.2 Nitroxides in Organic Synthesis
Book
Editors: Fensterbank, L. ; Ollivier, C.
Title: Free Radicals: Fundamentals and Applications in Organic Synthesis 1
Print ISBN: 9783132435520; Online ISBN: 9783132435537; Book DOI: 10.1055/b000000087
1st edition © 2021. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Reference Libraries
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.; Fürstner, A.; Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L
Type: Multivolume Edition
Abstract
This review describes selected methods using nitroxides such as TEMPO and AZADO for selective oxidative transformations including oxidation of alcohols and diols, N-alkylation of amines, C—H activation, C—C bond formation, and cross-coupling radical reactions.
Key words
radicals - nitroxides - oxidation - oxoammonium - alcohol oxidation - chemoselective oxidation - TEMPO - copper(I)/TEMPO catalyzed aerobic oxidation - Anelli protocol - persistent radical effect - C—C bond formation-
10 Shibuya M, Pichierri F, Tomizawa M, Nagasawa S, Suzuki I, Iwabuchi Y. Tetrahedron Lett. 2012; 53: 2070
-
19 Ni QZ, Daviso E, Can TV, Markhasin E, Jawla SK, Swager TM, Temkin RJ, Herzfeld J, Griffin RG. Acc. Chem. Res. 2013; 46: 1933
-
22 Soule BP, Hyodo F, Matsumoto K.-i, Simone NL, Cook JA, Krishna MC, Mitchell JB. Free Radical Biol. Med. 2007; 42: 1632
-
24 Sowers AM, McCombs JR, Wang Y, Paletta JT, Morton SW, Dreaden EC, Boska MD, Ottaviani MF, Hammond PT, Rajca A, Johnson JA. Nat. Commun. 2014; 5: 5460
- 25 Nitroxide-Mediated Polymerization: From Fundamentals to Applications in Materials Sciences. Gigmes D. RSC; Cambridge, UK 2016
- 30 Noir BLC, Catalysis from A to Z: A Concise Encyclopedia. Cornils B, Herrmann WA, Xu J.-H, Zanthoff H.-W. Wiley-VCH; Weinheim, Germany 2020
-
42 Leroi C, Bertin D, Dufils P.-E, Gigmes D, Marque S, Tordo P, Couturier J.-L, Guerret O, Ciufolini MA. Org. Lett. 2003; 5: 4943
-
46 Kafka F, Holan M, Hidasová D, Pohl R, Císařová I, Klepetářová B, Jahn U. Angew. Chem. Int. Ed. 2014; 53: 9944
-
56 Golubev VA, Rozantsev ÉG, Neiman MB. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1965; 14: 1898
-
71 Nakagami S, Akita T, Kiyohara D, Uchida Y, Tamura R, Nishiyama N. J. Phys. Chem. B 2018; 122: 7409
-
72 Amar M, Bar S, Iron MA, Toledo H, Tumanskii B, Shimon LJW, Botoshansky M, Fridman N, Szpilman AM. Nat. Commun. 2015; 6: 6070
-
75 Ikuma N, Tsue H, Tsue N, Shimono S, Uchida Y, Masaki K, Matsuoka N, Tamura R. Org. Lett. 2005; 7: 1797
-
79 Murakami K, Sasano Y, Tomizawa M, Shibuya M, Kwon E, Iwabuchi Y. J. Am. Chem. Soc. 2014; 136: 17591
-
122 Hayes EC, Porter TR, Barrows CJ, Kaminsky W, Mayer JM, Stoll S. J. Am. Chem. Soc. 2016; 138: 4132
-
123 Walroth RC, Miles KC, Lukens JT, MacMillan SN, Stahl SS, Lancaster KM. J. Am. Chem. Soc. 2017; 139: 13507
-
124 Ochen A, Whitten R, Aylott HE, Ruffell K, Williams GD, Slater F, Roberts A, Evans P, Steves JE, Sanganee MJ. Organometallics 2019; 38: 176
-
127 Sasano Y, Nagasawa S, Yamazaki M, Shibuya M, Park J, Iwabuchi Y. Angew. Chem. Int. Ed. 2014; 53: 3236
-
132 Díaz-Rodríguez A, Lavandera I, Kanbak-Aksu S, Sheldon RA, Gotar V, Gotor-Fernández V. Adv. Synth. Catal. 2012; 354: 3405
-
135 Dornan LM, Cao Q, Flanagan JCA, Crawford JJ, Cook MJ, Muldoon MJ. Chem. Commun. (Cambridge) 2013; 49: 6030
-
140 Kataoka K, Wachi K, Jin X, Suzuki K, Sasano Y, Iwabuchi Y, Hasegawa J.-y, Mizuno N, Yamaguchi K. Chem. Sci. 2018; 9: 4756
-
142 Könning D, Olbrisch T, Sypaseuth FD, Tzschucke CC, Christmann M. Chem. Commun. (Cambridge) 2014; 50: 5014
-
145 Flanagan JCA, Dornan LM, McLaughlin MG, McCreanor NG, Cook MJ, Muldoon MJ. Green Chem. 2012; 14: 1281
-
152 Matsumoto T, Ueno M, Kobayashi J, Miyamura H, Mori Y, Kobayashi S. Adv. Synth. Catal. 2007; 349: 531
-
153 Dijksman A, Marino-González A, Mairata i Payeras A, Arends IWCE, Sheldon RA. J. Am. Chem. Soc. 2001; 123: 6826
-
157 Miao C.-X, Wang J.-Q, Yu B, Cheng W.-G, Sun J, Chanfreau S, He L.-N, Zhang S.-J. Chem. Commun. (Cambridge) 2011; 47: 2697
-
161 Ma S, Liu J, Li S, Chen B, Cheng J, Kuang J, Liu Y, Wan B, Wang Y, Ye J, Yu Q, Yuan W, Yu S. Adv. Synth. Catal. 2011; 353: 1005
-
176 Chamorro-Arenas D, Osorio-Nieto U, Quintero L, Hernández-García L, Sartillo-Piscil F. J. Org. Chem. 2018; 83: 15333
-
188 Türkyilmaz F, Kehr G, Li J, Daniliuc CG, Tesch M, Studer A, Erker G. Angew. Chem. Int. Ed. 2016; 55: 1470
-
194 Michaud A, Gingras G, Morin M, Béland F, Ciriminna R, Avnir D, Pagliaro M. Org. Process Res. Dev. 2007; 11: 766
-
200 Beejapur HA, Giacalone F, Noto R, Franchi P, Lucarini M, Gruttadauria M. ChemCatChem 2013; 5: 2991