Applications of TEMPO in Synthesis

Thomas Vogler; Armido Studer

doi:10.1055/s-2008-1078445

REVIEW

Applications of TEMPO in Synthesis

Thomas Vogler, Armido Studer*
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Fax: +49(251)8336523; e-Mail: studer@uni-muenster.de;

Abstract

Alle Artikel dieser Rubrik

Abstract

This review describes the broad application of TEMPO and its derivatives in organic synthesis. Various reactions including oxidation of alcohols, sulfides and organometallic compounds are discussed. Moreover, the use of TEMPO as a stoichiometric or catalytic cooxidant in various transition-metal-mediated reactions is presented. The application of TEMPO as a carbon-radical trapping reagent in cascade reactions is discussed. Finally, the review article focuses on the application of TEMPO-derived alkoxyamines as thermal carbon-radical precursors in synthesis and in polymer chemistry.

1 Nitroxides

2 Oxidations

2.1 Oxidation of Alcohols

2.2 Oxidation of Sulfides and Hydrogen Abstractions

3 TEMPO as Trapping Reagent

4 Reaction of TEMPO with Organometallic Compounds

5 Carbon-Oxygen Bond Homolysis of Alkoxyamines

6 Conclusions

Key words

nitroxides - oxidations - radical chemistry - domino reactions - polymerizations

Volltext

Referenzen

References

1 Aurich HG. In Nitrones, nitronates and nitroxides Patai S. Rappoport Z. John Wiley & Sons; New York: 1989. p.313

2 Aurich HG. Hahn K. Stork K. Weiss W. Tetrahedron 1977, 33: 969

3 Fremy E. Ann. Chim. Phys. 1845, 15: 408

4 Piloty O. Schwerin B. Chem. Ber. 1901, 34: 2354

5a Wieland H. Roth K. Chem. Ber. 1920, 53: 210

5b Wieland H. Offenbächer M. Chem. Ber. 1914, 47: 2111

6 Lebedev OL. Kazarnovskii SN. Tr. Khim. Khim. Tekhnol. 1959, 2: 649 ; Chem. Abstr. 1962, 56, 15479f

7 Griller D. Ingold KU. Acc. Chem. Res. 1976, 9: 13

8 Novak I. Harrison LJ. Kovač B. Pratt LM. J. Org. Chem. 2004, 69: 7628

9 Volodarsky LB. Reznikov VA. Ovcharenko VI. Synthetic Chemisty of Stable Nitroxides CRC Press; Boca Raton (USA): 1994.

10a Nakatsuji S. Anzai H. J. Mater. Chem. 1997, 7: 2161

10b Caneschi A. Gatteschi D. Sessoli R. Rey P. Acc. Chem. Res. 1989, 22: 392

11a Qu J. Katsumata T. Satoh M. Wada J. Igarashi J. Mizoguchi K. Masuda T. Chem. Eur. J. 2007, 13: 7965

11b Qu J. Fujii T. Katsumata T. Suzuki Y. Shiotsuki M. Sanda F. Satoh M. Wada J. Masuda T. J. Polym. Sci. Part A: Polym. Chem. 2007, 45: 5431

11c Buhrmester C. Moshurchak LM. Wang RL. Dahn JR. J. Electrochem. Soc. 2006, 153: A1800

11d Katsumata T. Satoh M. Wada J. Shiotsuki M. Sanda F. Masuda T. Macromol. Rapid Commun. 2006, 27: 1206

11e Nishide H. Suga T. Electrochem. Soc. Interface 2005, 14: 32

12 Yonekuta Y. Susuki K. Oyaizu K. Honda K. Nishide H. J. Am. Chem. Soc. 2007, 129: 14128

13 Naik N. Braslau R. Tetrahedron 1998, 54: 667

14a Keana JFW. Chem. Rev. 1978, 78: 37

14b Ullman EF. Osiecki JH. Boocock DGB. Darcy R. J. Am. Chem. Soc. 1972, 94: 7049

14c Stone TJ. Buckman T. Nordio PL. McConnell HM. Proc. Natl. Acad. Sci. U.S.A. 1965, 54: 1010

15a Janzen EG. Zhang Y.-K. Haire DL. J. Am. Chem. Soc. 1994, 116: 3738

15b Janzen EG. Acc. Chem. Res. 1971, 4: 31

16 Sheldon RA. Arends IWCE. Adv. Synth. Catal. 2004, 346: 1051

17 Adam W. Saha-Möller CR. Ganeshpure PA. Chem. Rev. 2001, 101: 3499

18 de Nooy AEJ. Besemer AC. van Bekkum H. Synthesis 1996, 1153

19 Zhao M. Li J. Mano E. Song Z. Tschaen DM. Grabowski EJJ. Reider PJ. J. Org. Chem. 1999, 64: 2564

20 Schämann M. Schäfer HJ. Synlett 2004, 1601

21 Bailey WF. Bobbitt JM. Wiberg KB. J. Org. Chem. 2007, 72: 4504

22a Merbouh N. Bobbitt JM. Brückner C. Org. Prep. Proced. Int. 2004, 36: 1

22b Banwell MG. Bridges VS. Dupuche JR. Richards SL. Walter JM. J. Org. Chem. 1994, 59: 6338

23 Kashiwagi Y. Ikezoe H. Ono T. Synlett 2006, 69

24a Miller RA. Hoerrner RS. Org. Lett. 2003, 5: 285

24b Bolm C. Magnus AS. Hildebrand JP. Org. Lett. 2000, 2: 1173

24c Inokuchi T. Matsumoto S. Nishiyama T. Torii S. J. Org. Chem. 1990, 55: 462

25a Zhao X.-F. Zhang C. Synthesis 2007, 551

25b De Luca L. Giacomelli G. Masala S. Porcheddu A. J. Org. Chem. 2003, 68: 4999

25c Einhorn J. Einhorn C. Ratajczak F. Pierre J.-L. J. Org. Chem. 1996, 61: 7452

25d Cella JA. Kelley JA. Kenehan EF. J. Org. Chem. 1975, 40: 1860

26 De Mico A. Margarita R. Parlanti L. Vescovi A. Piancatelli G. J. Org. Chem. 1997, 62: 6974

27 Anelli PL. Biffi C. Montanari F. Quici S. J. Org. Chem. 1987, 52: 2559

28 Rychnovsky SD. Vaidyanathan R. J. Org. Chem. 1999, 64: 310

29 Lemoine S. Thomazeau C. Joannard D. Trombotto S. Descotes G. Bouchu A. Queneau Y. Carbohydr. Res. 2000, 326: 176

30a Bragd PL. Besemer AC. van Bekkum H. Carbohydr. Res. 2000, 328: 355

30b Isogai A. Kato Y. Cellulose 1998, 5: 153

30c Davis NJ. Flitsch SL. Tetrahedron Lett. 1993, 34: 1181

31 Caron S. Dugger RW. Gut Ruggeri S. Ragan JA. Brown Ripin DH. Chem. Rev. 2006, 106: 2943

32 Mandal M. Yun H. Dudley GB. Lin S. Tan DS. Danishefsky SJ. J. Org. Chem. 2005, 70: 10619

33a Kloth K. Brünjes M. Kunst E. Jöge T. Gallier F. Adibekian A. Kirschning A. Adv. Synth. Catal. 2005, 347: 1423

33b Tashino Y. Togo H. Synlett 2004, 2010

33c Brünjes M. Sourkouni-Argirusi G. Kirschning A. Adv. Synth. Catal. 2003, 345: 635

33d Sakuratani K. Togo H. Synthesis 2003, 21

33e Sourkouni-Argirusi G. Kirschning A. Org. Lett. 2000, 2: 3781

34a Cozzi F. Adv. Synth. Catal. 2006, 348: 1367

34b Benaglia M. Puglisi A. Cozzi F. Chem. Rev. 2003, 103: 3401

35 Gheorghe A. Cuevas-Yañez E. Horn J. Bannwarth W. Narsaiah B. Reiser O. Synlett 2006, 2767

36 Holczknecht O. Cavazzini M. Quici S. Shepperson I. Pozzi G. Adv. Synth. Catal. 2005, 347: 677

37 Wu X.-E. Ma L. Ding M.-X. Gao L.-X. Synlett 2005, 607

38 Jiang N. Ragauskas AJ. Tetrahedron Lett. 2005, 46: 3323

39 Ansari IA. Gree R. Org. Lett. 2002, 4: 1507

40 Karimi B. Biglari A. Clark JH. Budarin V. Angew. Chem. Int. Ed. 2007, 46: 7210

41a Michaud A. Gingras G. Morin M. Béland F. Ciriminna R. Avnir D. Pagliaro M. Org. Process Res. Dev. 2007, 11: 766

41b Testa ML. Ciriminna R. Hajji C. Zaballos Garcia E. Ciclosi M. Sepulveda Arques J. Pagliaro M. Adv. Synth. Catal. 2004, 346: 655

41c Ciriminna R. Bolm C. Fey T. Pagliaro M. Adv. Synth. Catal. 2002, 344: 159

41d Brunel D. Fajula F. Nagy JB. Deroide B. Verhoef MJ. Veum L. Peters JA. van Bekkum H. Appl. Catal. A 2001, 213: 73

41e Fey T. Fischer H. Bachmann S. Albert K. Bolm C. J. Org. Chem. 2001, 66: 8154

41f Bolm C. Fey T. Chem. Commun. 1999, 1795

42 Geneste F. Moinet C. Ababou-Girard S. Solal F. New J. Chem. 2005, 29: 1520

43 Kubota J. Ido T. Kuroboshi M. Tanaka H. Uchida T. Shimamura K. Tetrahedron 2006, 62: 4769

44a Gheorghe A. Matsuno A. Reiser O. Adv. Synth. Catal. 2006, 348: 1016

44b Pozzi G. Cavazzini M. Quici S. Benaglia M. Dell’Anna G. Org. Lett. 2004, 6: 441

44c Dijksman A. Arends IWCE. Sheldon RA. Chem. Commun. 2000, 271

45a Gilhespy M. Lok M. Baucherel X. Chem. Commun. 2005, 1085

45b Benaglia M. Puglisi A. Holczknecht O. Quici S. Pozzi G. Tetrahedron 2005, 61: 12058

46 Weik S. Nicholson G. Jung G. Rademann J. Angew. Chem. Int. Ed. 2001, 40: 1436

47a Figiel PJ. Leskelä M. Repo T. Adv. Synth. Catal. 2007, 349: 1173

47b Mannam S. Alamsetti SK. Sekar G. Adv. Synth. Catal. 2007, 349: 2253

47c Salinas Uber J. Vogels Y. van den Helder D. Mutikainen I. Turpeinen U. Fu WT. Roubeau O. Gamez P. Reedijk J. Eur. J. Inorg. Chem. 2007, 4197

47d Lu N. Lin Y.-C. Tetrahedron Lett. 2007, 48: 8823

47e Jiang N. Ragauskas AJ. J. Org. Chem. 2006, 71: 7087

47f Striegler S. Tetrahedron 2006, 62: 9109

47g Velusamy S. Srinivasan A. Punniyamurthy T. Tetrahedron Lett. 2006, 47: 923

47h Gamez P. Arends IWCE. Sheldon RA. Reedijk J. Adv. Synth. Catal. 2004, 346: 805

47i Ragagnin G. Betzemeier B. Quici S. Knochel P. Tetrahedron 2002, 58: 3985

47j Semmelhack MF. Schmid CR. Cortés DA. Chou CS. J. Am. Chem. Soc. 1984, 106: 3374

48 Minisci F. Recupero F. Pedulli GF. Lucarini M. J. Mol. Catal. A: Chem. 2003, 204-205: 63

49 Ben-Daniel R. Alsters P. Neumann R. J. Org. Chem. 2001, 66: 8650

50 Wang N. Liu R. Chen J. Liang X. Chem. Commun. 2005, 5322

51 Dijksman A. Marino-González A. Mairata i Payeras A. Arends IWCE. Sheldon RA. J. Am. Chem. Soc. 2001, 123: 6826

52 Cecchetto A. Fontana F. Minisci F. Recupero F. Tetrahedron Lett. 2001, 42: 6651

53a Sheldon RA. Arends IWCE. J. Mol. Catal. A: Chem. 2006, 251: 200

53b Arends IWCE. Li Y.-X. Ausan R. Sheldon RA. Tetrahedron 2006, 62: 6659

53c Fabbrini M. Galli C. Gentili P. J. Mol. Catal. B: Enzym. 2002, 16: 231

53d Fabbrini M. Galli C. Gentili P. Macchitella D. Tetrahedron Lett. 2001, 42: 7551

54 Sheldon RA. Arends IWCE. Ten Brink G.-J. Dijksman A. Acc. Chem. Res. 2002, 35: 774

55 Lenoir D. Angew. Chem. Int. Ed. 2006, 45: 3206

56a Xie Y. Mo W. Xu D. Shen Z. Sun N. Hu B. Hu X. J. Org. Chem. 2007, 72: 4288

56b Liu R. Dong C. Liang X. Wang X. Hu X. J. Org. Chem. 2005, 70: 729

56c Liu R. Liang X. Dong C. Hu X. J. Am. Chem. Soc. 2004, 126: 4112

57 Shibuya M. Tomizawa M. Suzuki I. Iwabuchi Y. J. Am. Chem. Soc. 2006, 128: 8412

58a Mitsudo K. Kumagai H. Takabatake F. Kubota J. Tanaka H. Tetrahedron Lett. 2007, 48: 8994

58b Palmisano G. Ciriminna R. Pagliaro M. Adv. Synth. Catal. 2006, 348: 2033

58c Semmelhack MF. Chou CS. Cortes DA. J. Am. Chem. Soc. 1983, 105: 4492

59a Schämann M. Schäfer HJ. Electrochim. Acta 2005, 50: 4956

59b Schämann M. Schäfer HJ. Eur. J. Org. Chem. 2003, 351

59c Schnatbaum K. Schäfer HJ. Synthesis 1999, 864

60 Arterburn JB. Tetrahedron 2001, 57: 9765

61 Kuroboshi M. Yoshihisa H. Cortona MN. Kawakami Y. Gao Z. Tanaka H. Tetrahedron Lett. 2000, 41: 8131

62 Calderón F. Synlett 2006, 657

63 Siedlecka R. Skarzewski J. Synthesis 1994, 401

64 Siedlecka R. Skarzewski J. Synlett 1996, 757

65 Huang J.-Y. Li S.-J. Wang Y.-G. Tetrahedron Lett. 2006, 47: 5637

66 Velusamy S. Kumar AV. Saini R. Punniyamurthy T. Tetrahedron Lett. 2005, 46: 3819

67 d’Acunzo F. Baiocco P. Fabbrini M. Galli C. Gentili P. Eur. J. Org. Chem. 2002, 4195

68a Palomo C. Oiarbide M. Landa A. Esnal A. Linden A. J. Org. Chem. 2001, 66: 4180

68b Palomo C. Oiarbide M. Esnal A. Landa A. Miranda JI. Linden A. J. Org. Chem. 1998, 63: 5838

69 Palomo C. Aizpurua JM. Cuevas C. Urchegui R. Linden A. J. Org. Chem. 1996, 61: 4400

70 Cho NS. Park CH. J. Korean Chem. Soc. 1995, 39: 657

71 Miyazawa T. Endo T. Tetrahedron Lett. 1986, 27: 3395

72 Kaizer J. Pap J. Speier G. Food Chem. 2005, 93: 425

73a Kashiwagi Y. Yanagisawa Y. Kurashima F. Anzai J.-i. Osa T. Bobbitt JM. Chem. Commun. 1996, 2745

73b Kashiwagi Y. Ono H. Osa T. Chem. Lett. 1993, 81

74 Coseri S. Ingold KU. Org. Lett. 2004, 6: 1641

75 Babiarz JE. Cunkle GT. DeBellis AD. Eveland D. Pastor SD. Shum SP. J. Org. Chem. 2002, 67: 6831

76 Johnston LJ. Tencer M. Scaiano JC. J. Org. Chem. 1986, 51: 2806

77 Pradhan PP. Bobbitt JM. Bailey WF. Org. Lett. 2006, 8: 5485

78 Breton T. Liaigre D. Belgsir EM. Tetrahedron Lett. 2005, 46: 2487

79a Yeung SK. Chan KS. Organometallics 2005, 24: 6426

79b Mak KW. Yeung SK. Chan KS. Organometallics 2002, 21: 2362

80a Chan KS. Li XZ. Dzik WI. de Bruin B. J. Am. Chem. Soc. 2008, 130: 2051

80b Feng M. Chan KS. Organometallics 2002, 21: 2743

80c Chan KS. Leung Y.-B. Inorg. Chem. 1994, 33: 3187

81 Lucarini M. Marchesi E. Pedulli GF. Chatgilialoglu C. J. Org. Chem. 1998, 63: 1687

82 Jones C. Rose RP. New J. Chem. 2007, 31: 1484

83 Gupta R. Borovik AS. J. Am. Chem. Soc. 2003, 125: 13234

84a Recupero F. Punta C. Chem. Rev. 2007, 107: 3800

84b Ishii Y. Sakaguchi S. Iwahama T. Adv. Synth. Catal. 2001, 343: 393

85 Nechab M. Kumar DN. Philouze C. Einhorn C. Einhorn J. Angew. Chem. Int. Ed. 2007, 46: 3080

86 Chen Y. Wang PG. Tetrahedron Lett. 2001, 42: 4955

87 d’Acunzo F. Baiocco P. Fabbrini M. Galli C. Gentili P. New J. Chem. 2002, 26: 1791

88 Sobek J. Martschke R. Fischer H. J. Am. Chem. Soc. 2001, 123: 2849

89a Bowry VW. Ingold KU. J. Am. Chem. Soc. 1992, 114: 4992

89b Beckwith ALJ. Bowry VW. Ingold KU. J. Am. Chem. Soc. 1992, 114: 4983

90 Wright PJ. English AM. J. Am. Chem. Soc. 2003, 125: 8655

91a Hoye AT. Davoren JE. Wipf P. Fink MP. Kagan VE. Acc. Chem. Res. 2008, 41: 87

91b Jiang J. Kurnikov I. Belikova NA. Xiao J. Zhao Q. Amoscato AA. Braslau R. Studer A. Fink MP. Greenberger JS. Wipf P. Kagan VE. J. Pharmacol. Exp. Ther. 2007, 320: 1050

91c Wipf P. Xiao J. Jiang J. Belikova NA. Tyurin VA. Fink MP. Kagan VE. J. Am. Chem. Soc. 2005, 127: 12460

92 Samuni A. Goldstein S. Russo A. Mitchell JB. Krishna MC. Neta P. J. Am. Chem. Soc. 2002, 124: 8719

93 Ban S. Nakagawa H. Suzuki T. Miyata N. Bioorg. Med. Chem. Lett. 2007, 17: 1451

94 Studer A. Chem. Soc. Rev. 2004, 33: 267

95 Dao J. Benoit D. Hawker CJ. J. Polym. Sci. Part A: Polym. Chem. 1998, 36: 2161

96a Henry-Riyad H. Tidwell TT. J. Phys. Org. Chem. 2003, 16: 559

96b Anderson JE. Casarini D. Corrie JET. Lunazzii L. J. Chem. Soc., Perkin Trans. 2 1993, 1299

97 Studer A. Angew. Chem. Int. Ed. 2000, 39: 1108

98a Ren T. Liu Y.-C. Guo Q.-X. Bull. Chem. Soc. Jpn. 1996, 69: 2935

98b Hunter DH. Barton DHR. Motherwell WJ. Tetrahedron Lett. 1984, 25: 603

99 Jahn U. Hartmann P. Dix I. Jones PG. Eur. J. Org. Chem. 2001, 3333

100a Boger DL. Boyce CW. J. Org. Chem. 2000, 65: 4088

100b Boger DL. McKie JA. J. Org. Chem. 1995, 60: 1271

101 Boger DL. Garbaccio RM. Jin Q. J. Org. Chem. 1997, 62: 8875

102 Inokuchi T. Kawafuchi H. Tetrahedron 2004, 60: 11969

103a Jahn U. Müller M. Aussieker S. J. Am. Chem. Soc. 2000, 122: 5212

103b Jahn U. Hartmann P. Dix I. Jones PG. Eur. J. Org. Chem. 2001, 3333

104 Goddard J.-P. Gomez C. Brebion F. Beauvière S. Fensterbank L. Malacria M. Chem. Commun. 2007, 2929

105 Heinrich MR. Wetzel A. Kirschstein M. Org. Lett. 2007, 9: 3833

106 Heinrich MR. Kirschstein MD. Tetrahedron Lett. 2006, 47: 2115

107 Sibi MP. Hasegawa M. J. Am. Chem. Soc. 2007, 129: 4124

108 Inokuchi T. Nakagawa K. Torii S. Tetrahedron Lett. 1995, 36: 3223

109 Tidwell TT. Eur. J. Org. Chem. 2006, 563

110 Allen AD. Fenwick MF. Henry-Riyad H. Tidwell TT. J. Org. Chem. 2001, 66: 5759

111 Allen AD. Cheng B. Fenwick MH. Huang W.-w. Missiha S. Tahmassebi D. Tidwell TT. Org. Lett. 1999, 1: 693

112 Sholle VD. Golubev VA. Rozantsev EG. Dokl. Akad. Nauk SSSR 1971, 200: 137 ; Chem. Abstr. 1972, 76, 25049e

113 Whitesides GM. Newirth TL. J. Org. Chem. 1975, 40: 3448

114 Nagashima T. Curran DP. Synlett 1996, 330

115 Dalko PI. Tetrahedron Lett. 1999, 40: 4035

116a Schaffner A.-P. Renaud P. Eur. J. Org. Chem. 2004, 2291

116b Ollivier C. Renaud P. Chem. Rev. 2001, 101: 3415

117 Baban JA. Goodchild NJ. Roberts BP. J. Chem. Soc., Perkin Trans. 2 1986, 157

118 Ollivier C. Chuard R. Renaud P. Synlett 1999, 807

119a Spikes GH. Peng Y. Fettinger JC. Steiner J. Power PP. Chem. Commun. 2005, 6041

119b Naka A. Hill NJ. West R. Organometallics 2004, 23: 6330

119c Forbes GC. Kennedy AR. Mulvey RE. Rodger PJA. Chem. Commun. 2001, 1400

120a Eaton SS. Eaton GR. Coord. Chem. Rev. 1988, 83: 29

120b Eaton SS. Eaton GR. Coord. Chem. Rev. 1978, 26: 207

121a Huang K.-W. Han JH. Cole AP. Musgrave CB. Waymouth RM. J. Am. Chem. Soc. 2005, 127: 3807

121b Huang K.-W. Waymouth RM. J. Am. Chem. Soc. 2002, 124: 8200

122 Vasbinder MJ. Bakac A. Inorg. Chem. 2007, 46: 2322

123 Zhang Z. Berg A. Levanon H. Fessenden RW. Meisel D. J. Am. Chem. Soc. 2003, 125: 7959

124 Lagunas A. Mairata i Payeras A. Jimeno C. Pericàs MA. Chem. Commun. 2006, 1307

125 Lagunas A. Mairata i Payeras A. Jimeno C. Pericàs MA. Org. Lett. 2005, 7: 3033

126 Ringwald M. Stürmer R. Brintzinger HH. J. Am. Chem. Soc. 1999, 121: 1524

127 Lam PYS. Vincent G. Clark CG. Deudon S. Jadhav PK. Tetrahedron Lett. 2001, 42: 3415

128 Chan DMT. Monaco KL. Wang R.-P. Winters MP. Tetrahedron Lett. 1998, 39: 2933

129 Lam PYS. Clark CG. Saubern S. Adams J. Winters MP. Chan DMT. Combs A. Tetrahedron Lett. 1998, 39: 2941

130 Evans DA. Katz JL. West TR. Tetrahedron Lett. 1998, 39: 2937

131 Vogler T. Studer A. Org. Lett. 2008, 10: 129

132a Studer A. Schulte T. Chem. Rec. 2005, 5: 27

132b Studer A. Chem. Eur. J. 2001, 7: 1159

132c Fischer H. Chem. Rev. 2001, 101: 3581

133a Molawi K. Schulte T. Siegenthaler KO. Wetter C. Studer A. Chem. Eur. J. 2005, 11: 2335