2.2 Catalytic Oxidations with Hypervalent Iodine

F. V. Singh; T. Wirth

Abstract

Hypervalent iodine chemistry is a very active research area in both organic synthesis and natural product chemistry. Hypervalent iodine reagents have been used to perform various oxidative transformations under mild reaction conditions. These reagents have received particular attention since the first reports, in 2005, that they can act as catalysts. Since then, various hypervalent iodine catalyzed oxidative functionalizations, such as oxidations of alcohols and phenols, α-functionalizations of carbonyl compounds, cyclizations, and rearrangements have been successfully achieved. Several catalytic reactions have been developed using hypervalent iodine reagents as catalysts, while in other reactions iodoarenes have been used as precatalyst to generate active iodine(III) or iodine(V) species in situ. This chapter highlights various aspects of hypervalent iodine-catalyzed oxidation reactions, including asymmetric variants.

Schlüsselwörter

catalytic oxidations - hypervalent iodine reagents - oxidants - stereoselective reactions

• 1 Wirth T. Angew. Chem. 2001; 113: 2893 Angew. Chem. Int. Ed. 2001; 40: 2812

• 2 Wirth T, In: Organic Synthesis Highlights V Schmalz H.-G, Wirth T. Wiley-VCH Weinheim, Germany 2003; 144

• 3 Hypervalent Iodine Chemistry. Wirth T. 224. Springer; Berlin 2003

• 4 Zhdankin VV. Chem. Rev. 2002; 102: 2523

• 5 Wirth T. Angew. Chem. 2005; 117: 3722 Angew. Chem. Int. Ed. 2005; 44: 3656

• 6 Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299

• 7 Zhdankin VV. ARKIVOC 2009; 1

• 8 Farooq U, Shah AA, Wirth T. Angew. Chem. 2009; 121: 1036 Angew. Chem. Int. Ed. 2009; 48: 1018

• 9 Zhdankin VV. J. Org. Chem. 2011; 76: 1185

• 10 Singh FV, Wirth T, In: Comprehensive Organic Synthesis Knochel P, Molander GA. Elsevier Oxford, UK 2014; 7. 881

• 11 Moriarty RM. J. Org. Chem. 2005; 70: 2893

• 12 Ladziata U, Zhdankin VV. Synlett 2007; 527

• 13 Merritt EA, Olofsson B. Angew. Chem. 2009; 121: 9214 Angew. Chem. Int. Ed. 2009; 48: 9052

• 14 Quideau S, Pouységu L, Deffieux D. Synlett 2008; 467

• 15 Uyanik M, Ishihara K. Chem. Commun. (Cambridge) 2009; 2086

• 16 Liang H, Ciufolini MA. Tetrahedron 2010; 66: 5884

• 17 Satam V, Harad A, Rajule R, Pati H. Tetrahedron 2010; 66: 7659

• 18 Guérard KC, Sabot C, Beaulieu M.-A, Giroux M.-A, Canesi S. Tetrahedron 2010; 66: 5893

• 19 Singh FV, Wirth T. Org. Lett. 2011; 13: 6504

• 20 Merritt EA, Olofsson B. Synthesis 2011; 517

• 21 Tinnis F, Stridfeldt E, Lundberg H, Adolfsson H, Olofsson B. Org. Lett. 2015; 17: 2688

• 22 Ghosh R, Stridfeldt E, Olofsson B. Chem.–Eur. J. 2014; 20: 8888

• 23 Ghosh R, Stridfeldt E, Jalalian N, Olofsson B. ChemistryOpen 2014; 3: 54

• 24 Brown M, Delorme M, Malmedy F, Malmgren J, Olofsson B, Wirth T. Synlett 2015; 26: 1573

• 25 Brand JP, González DF, Nicolai S, Waser J. Chem. Commun. (Cambridge) 2011; 47: 102

• 26 Wang H, Fan R. J. Org. Chem. 2010; 75: 6994

• 27 Moriarty RM, Tyagi S, Kinch M. Tetrahedron 2010; 66: 5801

• 28 Bose DS, Idrees M. Synthesis 2010; 393

• 29 Pardo LM, Tellitu I, Domínguez E. Synthesis 2010; 971

• 30 Du X, Chen H, Chen Y, Chen J, Liu Y. Synlett 2011; 1010

• 31 Wardrop DJ, Yermolina MV, Bowen EG. Synthesis 2012; 44: 1199

• 32 Singh FV, Wirth T. Synthesis 2012; 44: 1171

• 33 Paz NR, Santana AG, Francisco CG, Suárez E, González CC. Org. Lett. 2012; 14: 3388

• 34 Kajiyama D, Saitoh T, Yamaguchi S, Nishiyama S. Synthesis 2012; 44: 1667

• 35 Mizar P, Wirth T. Angew. Chem. 2014; 126: 6103 Angew. Chem. Int. Ed. 2014; 53: 5993

• 36 Qian G, Liu B, Tan Q, Zhang S, Xu B. Eur. J. Org. Chem. 2014; 4837

• 37 Mizar P, Burrelli A, Günther E, Söftje M, Farooq U, Wirth T. Chem.–Eur. J. 2014; 20: 13113

• 38 Yoshimura A, Koski SR, Fuchs JM, Saito A, Nemykin VN, Zhdankin VV. Chem.–Eur. J. 2015; 21: 5328

• 39 Singh FV, Wirth T. Synthesis 2013; 45: 2499

• 40 Richardson RD, Wirth T. Angew. Chem. 2006; 118: 4510 Angew. Chem. Int. Ed. 2006; 45: 4402

• 41 Ochiai M, Miyamoto K. Eur. J. Org. Chem. 2008; 4229

• 42 Dohi T, Kita Y. Chem. Commun. (Cambridge) 2009; 2073

• 43 Yusubov MS, Zhdankin VV. Mendeleev Commun. 2010; 20: 185

• 44 Singh FV, Wirth T. Chem.–Asian J. 2014; 9: 2499

• 45 Manna S, Antonchick AP. Angew. Chem. 2014; 126: 5608 Angew. Chem. Int. Ed. 2014; 53: 7324

• 46 Konnick MM, Hashiguchi BG, Devarajan D, Boaz NC, Gunnoe TB, Groves JT, Gunsalus N, Ess DH, Periana RA. Angew. Chem. 2014; 126: 10658 Angew. Chem. Int. Ed. 2014; 53: 10490

• 47 Mizar P, Laverny A, El-Sherbini M, Farid U, Brown M, Malmedy F, Wirth T. Chem.–Eur. J. 2014; 20: 9910

• 48 Kashiwa M, Sonoda M, Tanimori S. Eur. J. Org. Chem. 2014; 4720

• 49 Verma A, Patel S, Meenakshi, Kumar A, Yadav A, Kumar S, Jana S, Sharma S, Prasad CD, Kumar S. Chem. Commun. (Cambridge) 2015; 51: 1371

• 50 Ulmer A, Stodulski M, Kohlhepp SV, Patzelt C, Pöthig A, Bettray W, Gulder T. Chem.–Eur. J. 2015; 21: 1444

• 51 Yamamoto Y, Kawano Y, Toy PH, Togo H. Tetrahedron 2007; 63: 4680

• 52 Zhu C, Ji L, Wei Y. Monatsh. Chem. 2010; 141: 327

• 53 Herrerías CI, Zhang TY, Li C.-J. Tetrahedron Lett. 2006; 47: 13

• 54 Zhu C, Yoshimura A, Wei Y, Nemykin VN, Zhdankin VV. Tetrahedron Lett. 2012; 53: 1438

• 55 Yakura T, Ozono A. Adv. Synth. Catal. 2011; 353: 855

• 56 The Chemistry of the Quinonoid Compounds. Patai S, Rappoport Z. Wiley; Chichester, UK 1988. parts 1 and 2

• 57 Thomson RH. Naturally Occurring Quinones IV. Blackie Academic & Professional; London 1997

• 58 Dudfield PJ, In: Comprehensive Organic Synthesis Trost BM, Fleming I. Pergamon Oxford 1991; 7. 345

• 59 Ata A, Kerr RG, Moya CE, Jacobs RS. Tetrahedron 2003; 59: 4215

• 60 Wells G, Berry JM, Bradshaw TD, Burger AM, Seaton A, Wang B, Westwell AD, Stevens MFG. J. Med. Chem. 2003; 46: 532

• 61 Berry JM, Bradshaw TD, Fichtner I, Ren R, Schwalbe CH, Wells G, Chew E.-H, Stevens MFG, Westwell AD. J. Med. Chem. 2005; 48: 639

• 62 Lion CJ, Matthews CS, Wells G, Bradshaw TD, Stevens MFG, Westwell AD. Bioorg. Med. Chem. Lett. 2006; 16: 5005

• 63 Yakura T, Konishi T. Synlett 2007; 765

• 64 Yakura T, Tian Y, Yamauchi Y, Omoto M, Konishi T. Chem. Pharm. Bull. 2009; 57: 252

• 65 Yakura T, Yamauchi Y, Tian Y, Omoto M. Chem. Pharm. Bull. 2008; 56: 1632

• 66 Yakura T, Omoto M. Chem. Pharm. Bull. 2009; 57: 643

• 67 Yakura T, Omoto M, Yamauchi Y, Tian Y, Ozono A. Tetrahedron 2010; 66: 5833

• 68 Dohi T, Maruyama A, Yoshimura M, Morimoto K, Tohma H, Kita Y. Angew. Chem. 2005; 117: 6349 Angew. Chem. Int. Ed. 2005; 44: 6193

• 69 Dohi T, Maruyama A, Minamitsuji Y, Takenaga N, Kita Y. Chem. Commun. (Cambridge) 2007; 1224

• 70 Dohi T, Takenaga N, Fukushima K, Uchiyama T, Kato D, Shiro M, Fujioka H, Kita Y. Chem. Commun. (Cambridge) 2010; 46: 7697

• 71 Dohi T, Minamitsuji Y, Maruyama A, Hirose S, Kita Y. Org. Lett. 2008; 10: 3559

• 72 Ngatimin M, Frey R, Andrews C, Lupton DW, Hutt OE. Chem. Commun. (Cambridge) 2011; 47: 11778

• 73 Yu Z, Ju X, Wang J, Yu W. Synthesis 2011; 860

• 74 Xu Y, Hu TJ, Yan J. Chin. Chem. Lett. 2012; 23: 891

• 75 Xu Y, Yang Z, Hu J, Yan J. Synthesis 2013; 45: 370

• 76 Miyamoto K, Sei Y, Yamaguchi K, Ochiai M. J. Am. Chem. Soc. 2009; 131: 1382

• 77 Thottumkara PP, Vinod TK. Org. Lett. 2010; 12: 5640

• 78 Zhong W, Liu S, Yang J, Meng X, Li Z. Org. Lett. 2012; 14: 3336

• 79 Bigi MA, White MC. J. Am. Chem. Soc. 2013; 135: 7831

• 80 Xue Q, Xie J, Xu P, Hu K, Cheng Y, Zhu C. ACS Catal. 2013; 3: 1365

• 81 Thottumkara AP, Bowsher MS, Vinod TK. Org. Lett. 2005; 7: 2933

• 82 Schulze A, Giannis A. Synthesis 2006; 257

• 83 Bulman Page PC, Appleby LF, Buckley BR, Allin SM, McKenzie MJ. Synlett 2007; 1565

• 84 Uyanik M, Akakura M, Ishihara K. J. Am. Chem. Soc. 2009; 131: 251

• 85 Nicolaou KC, Baran PS, Zhong Y.-L, Barluenga S, Hunt KW, Kranich R, Vega JA. J. Am. Chem. Soc. 2002; 124: 2233

• 86 Nicolaou KC, Montagnon T, Baran PS, Zhong Y.-L. J. Am. Chem. Soc. 2002; 124: 2245

• 87 Nicolaou KC, Baran PS, Zhong Y.-L, Sugita K. J. Am. Chem. Soc. 2002; 124: 2212

• 88 Nicolaou KC, Sugita K, Baran PS, Zhong Y.-L. J. Am. Chem. Soc. 2002; 124: 2221

• 89 Nicolaou KC, Montagnon T, Baran PS. Angew. Chem. 2002; 114: 993 Angew. Chem. Int. Ed. 2002; 41: 1035

• 90 Plumb JB, Harper DJ. Chem. Eng. News 1990; 68: 3

• 91 Moorthy JN, Senapati K, Parida KN, Jhulki S, Sooraj K, Nair NN. J. Org. Chem. 2011; 76: 9593

• 92 Seth S, Jhulki S, Moorthy JN. Eur. J. Org. Chem. 2013; 2445

• 93 Miura T, Nakashima K, Tada N, Itoh A. Chem. Commun. (Cambridge) 2011; 47: 1875

• 94 Koposov AY, Litvinov DN, Zhdankin VV, Ferguson MJ, McDonald R, Tykwinski RR. Eur. J. Org. Chem. 2006; 4791

• 95 Drouet F, Masson G, Zhu J. Org. Lett. 2013; 15: 2854

• 96 Mu R, Liu Z, Yang Z, Liu Z, Wu L, Liu Z.-L. Adv. Synth. Catal. 2005; 347: 1333

• 97 Yusubov MS, Nemykin VN, Zhdankin VV. Tetrahedron 2010; 66: 5745

• 98 Chen J.-M, Zeng X.-M, Middleton K, Yusubov MS, Zhdankin VV. Synlett 2011; 1613

• 99 Yusubov MS, Zagulyaeva AA, Zhdankin VV. Chem.–Eur. J. 2009; 15: 11091

• 100 Zeng X.-M, Chen J.-M, Middleton K, Zhdankin VV. Tetrahedron Lett. 2011; 52: 5652

• 101 Uyanik M, Mutsuga T, Ishihara K. Molecules 2012; 17: 8604

• 102 Ojha LR, Kudugunti S, Maddukuri PP, Kommareddy A, Gunna MR, Dokuparthi P, Gottam HB, Botha KK, Parapati DR, Vinod TK. Synlett 2009; 117

• 103 Cui L.-Q, Liu K, Zhang C. Org. Biomol. Chem. 2011; 9: 2258

• 104 Para A, Reboredo S. Chem.–Eur. J. 2013; 19: 17244

• 105 Liang H, Ciufolini MA. Angew. Chem. 2011; 123: 12051 Angew. Chem. Int. Ed. 2011; 50: 11849

• 106 Berthiol F. Synthesis 2015; 47: 587

• 107 Kumar R, Wirth T. Top. Curr. Chem. 2016; 373: 243

• 108 Dohi T, Maruyama A, Takenaga N, Senami K, Minamitsuji Y, Fujioka H, Caemmerer SB, Kita Y. Angew. Chem. 2008; 120: 3847 Angew. Chem. Int. Ed. 2008; 47: 3787

• 109 Uyanik M, Yasui T, Ishihara K. Tetrahedron 2010; 66: 5841

• 110 Uyanik M, Yasui T, Ishihara K. Angew. Chem. 2010; 122: 2221 Angew. Chem. Int. Ed. 2010; 49: 2175

• 111 Uyanik M, Yasui T, Ishihara K. Angew. Chem. 2013; 125: 9385 Angew. Chem. Int. Ed. 2013; 52: 9215

• 112 Dohi T, Takenaga N, Nakae T, Toyoda Y, Yamasaki M, Shiro M, Fujioka H, Maruyama A, Kita Y. J. Am. Chem. Soc. 2013; 135: 4558

• 113 Quideau S, Lyvinec G, Marguerit M, Bathany K, Ozanne-Beaudenon A, Buffeteau T, Cavagnat D, Chénedé A. Angew. Chem. 2009; 121: 4675 Angew. Chem. Int. Ed. 2009; 48: 4605

• 114 Volp KA, Harned AM. Chem. Commun. (Cambridge) 2013; 49: 3001

• 115 Fujita M, Mori K, Shimogaki M, Sugimura T. Org. Lett. 2012; 14: 1294