11 Oxidation of Amines and N-Hetarenes

N. Jiao; Z. Li

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.

Schlüsselwörter

oxidation of amines - oxidation of hetarenes - organometallic catalysis - photocatalysis - biomimetic catalysis

• 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

• 3 Choi H, Doyle MP. Chem. Commun. (Cambridge) 2007; 745

• 4 Wang J.-R, Fu Y, Zhang B.-B, Cui X, Liu L, Guo Q.-X. Tetrahedron Lett. 2006; 47: 8293

• 5 Aschwanden L, Panella B, Rossbach P, Keller B, Baiker A. ChemCatChem 2009; 1: 111

• 6 So M.-H, Liu Y, Ho C.-M, Che C.-M. Chem.–Asian J. 2009; 4: 1551

• 7 Yuan H, Yoo W.-J, Miyamura H, Kobayashi S. J. Am. Chem. Soc. 2012; 134: 13970

• 8 Furukawa S, Suga A, Komatsu T. Chem. Commun. (Cambridge) 2014; 50: 3277

• 9 Zhu B, Angelici RJ. Chem. Commun. (Cambridge) 2007; 2157

• 10 Zhu B, Lazar M, Trewyn BG, Angelici RJ. J. Catal. 2008; 260: 1

• 11 Patil RD, Adimurthy S. Adv. Synth. Catal. 2011; 353: 1695

• 12 Marui K, Nomoto A, Ueshima M, Ogawa A. Tetrahedron Lett. 2015; 56: 1200

• 13 Srogl J, Voltrova S. Org. Lett. 2009; 11: 843

• 14 Tang R, Diamond SE, Neary N, Mares F. J. Chem. Soc., Chem. Commun. 1978; 562

• 15 Yamaguchi K, Mizuno N. Angew. Chem. Int. Ed. 2003; 42: 1480

• 16 Mori K, Yamaguchi K, Mizugaki T, Ebitani K, Kaneda K. Chem. Commun. (Cambridge) 2001; 461

• 17 Venkatesan S, Kumar AS, Lee J.-F, Chan T.-S, Zen J.-M. Chem.–Eur. J. 2012; 18: 6147

• 18 Cristian L, Nica S, Pavel OD, Mihailciuc C, Almasan V, Coman SM, Hardacre C, Parvulescu VI. Catal. Sci. Technol. 2013; 3: 2646

• 19 Pavel OD, Goodrich P, Cristian L, Coman SM, Pârvulescu VI, Hardacre C. Catal. Sci. Technol. 2015; 5: 2696

• 20 Li F, Chen J, Zhang Q, Wang Y. Green Chem. 2008; 10: 553

• 21 Kim J, Stahl SS. ACS Catal. 2013; 3: 1652

• 22 Jagadeesh RV, Junge H, Beller M. ChemSusChem 2015; 8: 92

• 23 Zhang J, Wang Z, Yang Y, Wan C, Zheng X, Wang Z. Green Chem. 2009; 11: 1973

• 24 Reddy JS, Sayari A. Catal. Lett. 1994; 28: 263

• 25 Joseph R, Ravindranathan T, Sudalai A. Tetrahedron Lett. 1995; 36: 1903

• 26 Suzuki K, Watanabe T, Murahashi S.-I. Angew. Chem. Int. Ed. 2008; 47: 2079

• 27 Suzuki K, Watanabe T, Murahashi S.-I. J. Org. Chem. 2013; 78: 2301

• 28 Yu J, Cao X, Lu M. Tetrahedron Lett. 2014; 55: 5751

• 29 Yu J, Lu M. Synlett 2014; 25: 1873

• 30 Tollari S, Cuscela M, Porta F. J. Chem. Soc., Chem. Commun. 1993; 1510

• 31 Biradar AV, Kotbagi TV, Dongare MK, Umbarkar SB. Tetrahedron Lett. 2008; 49: 3616

• 32 Møller ER, Jørgensen KA. J. Am. Chem. Soc. 1993; 115: 11814

• 33 Sakaue S, Tsubakino T, Nishiyama Y, Ishii Y. J. Org. Chem. 1993; 58: 3633

• 34 Defoin A. Synthesis 2004; 706

• 35 Bordoloi A, Halligudi SB. Adv. Synth. Catal. 2007; 349: 2085

• 36 Zhao D, Johansson M, Bäckvall J.-E. Eur. J. Org. Chem. 2007; 4431

• 37 Zhu Z, Espenson JH. J. Org. Chem. 1995; 60: 1326

• 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

• 41 Firouzabadi H, Iranpoor N, Amani K. Green Chem. 2001; 3: 131

• 42 Reddy KR, Maheswari CU, Venkateshwar M, Kantam ML. Adv. Synth. Catal. 2009; 351: 93

• 43 Sheng MN, Zajacek JG. J. Org. Chem. 1968; 33: 588

• 44 Choudary BM, Bharathi B, Reddy CV, Kantam ML, Raghavan KV. Chem. Commun. (Cambridge) 2001; 1736

• 45 Gopiraman M, Bang H, Babu SG, Wei K, Karvembu R, Kim IS. Catal. Sci. Technol. 2014; 4: 2099

• 46 Rout L, Punniyamurthy T. Adv. Synth. Catal. 2005; 347: 1958

• 47 Limnios D, Kokotos CG. Chem.–Eur. J. 2014; 20: 559

• 48 Theodorou A, Limnios D, Kokotos CG. Chem.–Eur. J. 2015; 21: 5238

• 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

• 51 Murahashi S.-I, Mitsui H, Shiota T, Tsuda T, Watanabe S. J. Org. Chem. 1990; 55: 1736

• 52 Marcantoni E, Petrini M, Polimanti O. Tetrahedron Lett. 1995; 36: 3561

• 53 Choudary BM, Bharathi B, Reddy CV, Kantam ML. Green Chem. 2002; 4: 279

• 54 Goti A, Nannelli L. Tetrahedron Lett. 1996; 37: 6025

• 55 Khatri PK, Choudhary S, Singh R, Jain SL, Khatri OP. Dalton Trans. 2014; 43: 8054

• 56 Reddy JS, Jacobs PA. Catal. Lett. 1996; 37: 213

• 57 Zonta C, Cazzola E, Mba M, Licini G. Adv. Synth. Catal. 2008; 350: 2503

• 58 Nikbakht F, Heydari A, Saberi D, Azizi K. Tetrahedron Lett. 2013; 54: 6520

• 59 Forcato M, Nugent WA, Licini G. Tetrahedron Lett. 2003; 44: 49

• 60 Forcato M, Mba M, Nugent WA, Licini G. Eur. J. Org. Chem. 2010; 740

• 61 Abrantes M, Gonçalves IS, Pillinger M, Vurchio C, Cordero FM, Brandi A. Tetrahedron Lett. 2011; 52: 7079

• 62 Lin Y.-M, Miller MJ. J. Org. Chem. 2001; 66: 8282

• 63 Heydari A, Aslanzadeh S. Adv. Synth. Catal. 2005; 347: 1223

• 64 Colladon M, Scarso A, Strukul G. Green Chem. 2008; 10: 793

• 65 Reppe W, Kröper H. Justus Liebigs Ann. Chem. 1953; 582: 38

• 66 Davis GT, Rosenblatt DH. Tetrahedron Lett. 1968; 4085

• 67 Murahashi S.-I, Naota T, Yonemura K. J. Am. Chem. Soc. 1988; 110: 8256

• 68 Wang J.-R, Liu L, Wang Y.-F, Zhang Y, Deng W, Guo Q.-X. Tetrahedron Lett. 2005; 46: 4647

• 69 Nakayama H, Itoh A. Synlett 2008; 675

• 70 Itoh I, Matsusaki Y, Fujiya A, Tada N, Miura T, Itoh A. Tetrahedron Lett. 2014; 55: 3160

• 71 Wang Y, Kobayashi H, Yamaguchi K, Mizuno N. Chem. Commun. (Cambridge) 2012; 48: 2642

• 72 Yan X, Fang K, Liu H, Xi C. Chem. Commun. (Cambridge) 2013; 49: 10650

• 73 Klobukowski ER, Mueller ML, Angelici RJ, Woo LK. ACS Catal. 2011; 1: 703

• 74 Preedasuriyachai P, Chavasiri W, Sakurai H. Synlett 2011; 1121

• 75 Genovino J, Lütz S, Sames D, Touré BB. J. Am. Chem. Soc. 2013; 135: 12346

• 76 Kim JW, Yamaguchi K, Mizuno N. Angew. Chem. Int. Ed. 2008; 47: 9249

• 77 Radu S. Stud. Cercet. Chim. 1972; 20: 1287

• 78 Hodgson HH. Chem. Rev. 1947; 40: 251

• 79 Stowell JC, Lau CM. J. Org. Chem. 1986; 51: 1614

• 80 Suresh S, Joseph R, Jayachandran B, Pol AV, Vinod MP, Sudalai A, Sonawane HR, Ravindranathan T. Tetrahedron 1995; 51: 11305

• 81 Murray RW, Iyanar K, Chen J, Wearing JT. Tetrahedron Lett. 1996; 37: 805

• 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

• 84 Benedini F, Nali M, Rindone B, Tollari S, Cenini S, La Monica G, Porta F. J. Mol. Catal. 1984; 34: 155

• 85 Grirrane A, Corma A, García H. Science (Washington, D. C.) 2008; 322: 1661

• 86 Pérez Y, Aprile C, Corma A, García H. Catal. Lett. 2010; 134: 204

• 87 Lu W, Xi C. Tetrahedron Lett. 2008; 49: 4011

• 88 Zhang M, Zhang R, Zhang A.-Q, Li X, Liang H. Synth. Commun. 2009; 39: 3428

• 89 Zhang C, Jiao N. Angew. Chem. Int. Ed. 2010; 49: 6174

• 90 Hu Z, Kerton FM. Org. Biomol. Chem. 2012; 10: 1618

• 91 Cai S, Rong H, Yu X, Liu X, Wang D, He W, Li Y. ACS Catal. 2013; 3: 478

• 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

• 93 Zhu Y, Shi Y. Org. Lett. 2013; 15: 1942

• 94 Lang X, Ji H, Chen C, Ma W, Zhao J. Angew. Chem. Int. Ed. 2011; 50: 3934

• 95 Lang X, Ma W, Zhao Y, Chen C, Ji H, Zhao J. Chem.–Eur. J. 2012; 18: 2624

• 96 Li N, Lang X, Ma W, Ji H, Chen C, Zhao J. Chem. Commun. (Cambridge) 2013; 49: 5034

• 97 Rueping M, Vila C, Szadkowska A, Koenigs RM, Fronert J. ACS Catal. 2012; 2: 2810

• 98 Naya S, Kimura K, Tada H. ACS Catal. 2013; 3: 10

• 99 Yang X.-J, Chen B, Li X.-B, Zheng L.-Q, Wu L.-Z, Tung C.-H. Chem. Commun. (Cambridge) 2014; 50: 6664

• 100 Ovoshchnikov DS, Donoeva BG, Golovko VB. ACS Catal. 2015; 5: 34

• 101 Jiang G, Chen J, Huang J.-S, Che C.-M. Org. Lett. 2009; 11: 4568

• 102 Yuan B, Chong R, Zhang B, Li J, Liu Y, Li C. Chem. Commun. (Cambridge) 2014; 50: 15593

• 103 Wu Y, Yuan B, Li M, Zhang W.-H, Liu Y, Li C. Chem. Sci. 2015; 6: 1873

• 104 Ushakov DB, Plutschack MB, Gilmore K, Seeberger PH. Chem.–Eur. J. 2015; 21: 6528

• 105 Colonna S, Gaggero N, Drabowicz J, Łyżwa P, Mikołajczyk M. Chem. Commun. (Cambridge) 1999; 1787

• 106 Ottolina G, Bianchi S, Belloni B, Carrea G, Danieli B. Tetrahedron Lett. 1999; 40: 8483

• 107 Colonna S, Pironti V, Pasta P, Zambianchi F. Tetrahedron Lett. 2003; 44: 869

• 108 Colonna S, Pironti V, Carrea G, Pasta P, Zambianchi F. Tetrahedron 2004; 60: 569

• 109 Ball S, Bruice TC. J. Am. Chem. Soc. 1979; 101: 4017

• 110 Ball S, Bruice TC. J. Am. Chem. Soc. 1980; 102: 6498

• 111 Yoneda F, Nakagawa K. J. Chem. Soc., Chem. Commun. 1980; 878

• 112 Imada Y, Iida H, Ono S, Masui Y, Murahashi S.-I. Chem.–Asian J. 2006; 1: 136

• 113 Murahashi S.-I, Oda T, Masui Y. J. Am. Chem. Soc. 1989; 111: 5002

• 114 Bergstad K, Bäckvall J.-E. J. Org. Chem. 1998; 63: 6650

• 115 Wendlandt AE, Stahl SS. Org. Lett. 2012; 14: 2850

• 116 Qin Y, Zhang L, Lv J, Luo S, Cheng J.-P. Org. Lett. 2015; 17: 1469

• 117 Largeron M, Fleury M.-B. Angew. Chem. Int. Ed. 2012; 51: 5409

• 118 Largeron M, Neudorffer A, Fleury M.-B. Angew. Chem. Int. Ed. 2003; 42: 1026

• 119 Largeron M, Chiaroni A, Fleury M.-B. Chem.–Eur. J. 2008; 14: 996

• 120 Samec JSM, Éll AH, Bäckvall J.-E. Chem.–Eur. J. 2005; 11: 2327

• 121 Wendlandt AE, Stahl SS. J. Am. Chem. Soc. 2014; 136: 506

• 122 Kobayashi Y, Kumadaki I, Sato H, Sekine Y, Hara T. Chem. Pharm. Bull. 1974; 22: 2097

• 123 Copéret C, Adolfsson H, Khuong T.-AV, Yudin AK, Sharpless KB. J. Org. Chem. 1998; 63: 1740

• 124 Yamaguchi K, Mizugaki T, Ebitani K, Kaneda K. New J. Chem. 1999; 23: 799

• 125 Veerakumar P, Balakumar S, Velayudham M, Lu K.-L, Rajagopal S. Catal. Sci. Technol. 2012; 2: 1140

• 126 Larionov OV, Stephens D, Mfuh AM, Arman HD, Naumova AS, Chavez G, Skenderi B. Org. Biomol. Chem. 2014; 12: 3026

• 127 Ullrich R, Dolge C, Kluge M, Hofrichter M. FEBS Lett. 2008; 582: 4100

• 128 Ding Y, Zhao W, Song W, Zhang Z, Ma B. Green Chem. 2011; 13: 1486

• 129 Ding Y, Zhao W. J. Mol. Catal. A: Chem. 2011; 337: 45

• 130 Zhang Z, Zhu Q, Ding Y. Synth. Commun. 2013; 43: 1211

• 131 Zhao W, Yang C. New J. Chem. 2013; 37: 1867

• 132 Zhao W, Yang C, Ding Y, Ma B. New J. Chem. 2013; 37: 2614

• 133 Yang C, Zhao W, Cheng Z, Luo B, Bi D. RSC Adv. 2015; 5: 36809

• 134 Gillard RD, Hall DPJ. J. Chem. Soc., Chem. Commun. 1988; 1163

• 135 Li Z, Huang X, Chen F, Zhang C, Wang X, Jiao N. Org. Lett. 2015; 17: 584

• 136 Kiener A, Glöckler R, Heinzmann K. J. Chem. Soc., Perkin Trans. 1 1993; 1201

• 137 Kang P, Foote CS. J. Am. Chem. Soc. 2002; 124: 9629

• 138 Liu Q, Wu P, Yang Y, Zeng Z, Liu J, Yi H, Lei A. Angew. Chem. Int. Ed. 2012; 51: 4666

• 139 Wang X, Gallardo-Donaire J, Martin R. Angew. Chem. Int. Ed. 2014; 53: 11084

• 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

• 142 Carvalho CMB, Neves MGPMS, Tomé AC, Paz FAA, Silva AMS, Cavaleiro JAS. Org. Lett. 2011; 13: 130

• 143 Lazzaro F, Crucianelli M, De Angelis F, Neri V, Saladino R. Tetrahedron Lett. 2004; 45: 9237

• 144 Perez DI, Grau MM, Arends IWCE, Hollmann F. Chem. Commun. (Cambridge) 2009; 6848

• 145 Chen S, Liu Z, Shi E, Chen L, Wei W, Li H, Cheng Y, Wan X. Org. Lett. 2011; 13: 2274

• 146 Yadav JS, Reddy BVS, Reddy CS, Krishna AD. Synthesis 2007; 693

• 147 Bhat V, Rawal VH. Chem. Commun. (Cambridge) 2011; 47: 9705

• 148 Kumar CNSSP, Devi CL, Rao VJ, Palaniappan S. Synlett 2008; 2023

• 149 Sriram R, Kumar CNSSP, Raghunandan N, Ramesh V, Sarangapani M, Rao VJ. Synth. Commun. 2012; 42: 3419

• 150 Boissel V, Simpkins NS, Bhalay G. Tetrahedron Lett. 2009; 50: 3283

• 151 Kong Y.-B, Zhu J.-Y, Chen Z.-W, Liu L.-X. Can. J. Chem. 2014; 92: 269

• 152 Nishida Y, Ito S. J. Chem. Soc., Chem. Commun. 1995; 1211

• 153 Fleming AM, Kannan A, Muller JG, Liao Y, Burrows CJ. J. Org. Chem. 2011; 76: 7953

• 154 Sheu C, Kang P, Khan S, Foote CS. J. Am. Chem. Soc. 2002; 124: 3905

• 155 Choi S, Cooley RB, Hakemian AS, Larrabee YC, Bunt RC, Maupas SD, Muller JG, Burrows CJ. J. Am. Chem. Soc. 2004; 126: 591

• 156 Saladino R, Carlucci P, Danti MC, Crestini C, Mincione E. Tetrahedron 2000; 56: 10031

• 157 Saladino R, Neri V, Checconi P, Celestino I, Nencioni L, Palamara AT, Crucianelli M. Chem.–Eur. J. 2013; 19: 2392

• 158 Saladino R, Neri V, Crestini C, Tagliatesta P. J. Mol. Catal. A: Chem. 2004; 214: 219