Muñiz, K.: 2018 Science of Synthesis, 2017/4: Catalytic Oxidation in Organic Synthesis DOI: 10.1055/sos-SD-225-00339
Catalytic Oxidation in Organic Synthesis

11 Oxidation of Amines and N-Hetarenes

More Information

Book

Editor: Muñiz, K.

Authors: Andries-Ulmer, A.; Bellina, F.; Berkessel, A.; Borrell, M.; Caballero, A.; Calleja, P.; Chemler, S. R.; Chen, P.; Costas, M.; Díaz-Requejo, M. M.; Dorel, R.; Dornan, L. M.; Ebner, D. C.; Echavarren, A. M.; Engler, H.; Esguerra, K. V. N.; Farràs, P.; Funes-Ardoiz, I.; Garrido-Barros, P.; Gimbert-Suriñach, C.; Gómez-Arrayas, R.; Griesbeck, A. G.; Gulder, T.; Hughes, N. L.; Ikariya, T.; Ishihara, K.; Jiao, N.; Kayaki, Y.; Kleczka, M.; Leuther, T. M.; Li, Z.; Liu, G.; Llobet, A.; Lumb, J.-P.; Martínez, C.; Maseras, F.; Muldoon, M. J.; Muñiz, K.; Park, N.; Patel, H. H.; Perego, L. A.; Pérez, P. J.; Race, N. J.; Rodríguez, N.; Sigman, M. S.; Sillner, S.; Singh, F. V.; Stoltz, B. M.; Uyanik, M.; Vicens, L.; Wdowik, T.; Wirth, T.; Wright, A. C.

Title: Catalytic Oxidation in Organic Synthesis

Print ISBN: 9783132012318; Online ISBN: 9783132403710; Book DOI: 10.1055/b-003-129345

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.; Koch, G.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

 


Abstract

The oxidation of amines and hetarenes are significant transformations that have been widely applied in synthetic organic chemistry. In this chapter, the oxidation of primary, secondary, and tertiary amines, affording imines, nitriles, amides, carbonyls, oximes, nitro compounds, diazenes and their oxides, nitrones, hydrazines, and N-oxides, as well as the oxidation of hetarenes including pyridines, azoles, pyrroles, indoles, guanines, and adenines, are comprehensively discussed. In addition to traditional organometallic catalysis to fulfill these oxidation reactions, some advanced approaches such as photocatalysis, biochemical catalysis, and biomimetic catalysis are also described.

 
  • 1 Murahashi S.-I, Naota T, Taki H. J. Chem. Soc., Chem. Commun. 1985; 613
  • 2 Maruyama K, Kusukawa T, Higuchi Y, Nishinaga A. Chem. Lett. 1991; 1093
  • 9 Zhu B, Angelici RJ. Chem. Commun. (Cambridge) 2007; 2157
  • 14 Tang R, Diamond SE, Neary N, Mares F. J. Chem. Soc., Chem. Commun. 1978; 562
  • 16 Mori K, Yamaguchi K, Mizugaki T, Ebitani K, Kaneda K. Chem. Commun. (Cambridge) 2001; 461
  • 30 Tollari S, Cuscela M, Porta F. J. Chem. Soc., Chem. Commun. 1993; 1510
  • 36 Zhao D, Johansson M, Bäckvall J.-E. Eur. J. Org. Chem. 2007; 4431
  • 38 Tollari S, Vergani D, Banfi S, Porta F. J. Chem. Soc., Chem. Commun. 1993; 442
  • 39 Jayachandran B, Sasidharan M, Sudalai A, Ravindranathan T. J. Chem. Soc., Chem. Commun. 1995; 1523
  • 40 Krohn K, Küpke J. Eur. J. Org. Chem. 1998; 679
  • 44 Choudary BM, Bharathi B, Reddy CV, Kantam ML, Raghavan KV. Chem. Commun. (Cambridge) 2001; 1736
  • 49 Riley DP. J. Chem. Soc., Chem. Commun. 1983; 1530
  • 50 Mitsui H, Zenki S, Shiota T, Murahashi S.-I. J. Chem. Soc., Chem. Commun. 1984; 874
  • 60 Forcato M, Mba M, Nugent WA, Licini G. Eur. J. Org. Chem. 2010; 740
  • 66 Davis GT, Rosenblatt DH. Tetrahedron Lett. 1968; 4085
  • 69 Nakayama H, Itoh A. Synlett 2008; 675
  • 74 Preedasuriyachai P, Chavasiri W, Sakurai H. Synlett 2011; 1121
  • 82 Gebhardt C, Priewisch B, Irran E, Rück-Braun K. Synthesis 2008; 1889
  • 83 Benedini F, Gallani G, Nali M, Rindone B, Tollari S. J. Chem. Soc., Perkin Trans. 2 1985; 1963
  • 92 Ma H, Li W, Wang J, Xiao G, Gong Y, Qi C, Feng Y, Li X, Bao Z, Cao W, Sun Q, Veaceslav C, Wang F, Lei Z. Tetrahedron 2012; 68: 8358
  • 105 Colonna S, Gaggero N, Drabowicz J, Łyżwa P, Mikołajczyk M. Chem. Commun. (Cambridge) 1999; 1787
  • 111 Yoneda F, Nakagawa K. J. Chem. Soc., Chem. Commun. 1980; 878
  • 134 Gillard RD, Hall DPJ. J. Chem. Soc., Chem. Commun. 1988; 1163
  • 136 Kiener A, Glöckler R, Heinzmann K. J. Chem. Soc., Perkin Trans. 1 1993; 1201
  • 140 Crossley MJ, Burn PL, Langford SJ, Pyke SM, Stark AG. J. Chem. Soc., Chem. Commun. 1991; 1567
  • 141 Khoury T, Crossley MJ. Chem. Commun. (Cambridge) 2007; 4851
  • 144 Perez DI, Grau MM, Arends IWCE, Hollmann F. Chem. Commun. (Cambridge) 2009; 6848
  • 146 Yadav JS, Reddy BVS, Reddy CS, Krishna AD. Synthesis 2007; 693
  • 148 Kumar CNSSP, Devi CL, Rao VJ, Palaniappan S. Synlett 2008; 2023
  • 152 Nishida Y, Ito S. J. Chem. Soc., Chem. Commun. 1995; 1211