Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis

Ivan A. Shuklov; Natalia V. Dubrovina; Armin Börner

doi:10.1055/s-2007-983902

REVIEW

Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis

Ivan A. Shuklov*^a, Natalia V. Dubrovina^a, Armin Börner*^a,b
^a Leibniz-Institut für Katalyse, Universität Rostock e.V., A.-Einstein-Str. 29a, 18059 Rostock, Germany
^b Institute of Organic Chemistry, University of Rostock, A.-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)12815202 ; e-Mail: ivan.shuklov@catalysis.de; e-Mail: armin.boerner@catalysis.de;

Abstract

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Abstract

The use of fluorinated alcohols as solvents, cosolvents or additives in homogeneous catalysis is reviewed. The effect of these particular compounds on efficiency, regioselectivity and stereoselectivity of metal-catalyzed reactions, as well as on reactions mediated by organocatalysts, is described. Where available in several cases, the effect of fluorous alcohols on the catalytic mechanism is analyzed in detail and rationalized by their unique physical and chemical properties. In most instances, a comparison to the effect of commonly employed solvents is elaborated.

1 Introduction

2 Physical Properties of Fluorinated Alcohols

3 Applications in Homogeneous Catalysis

3.1 Reduction Reactions

3.2 Oxidation Reactions

3.3 Carbon-Carbon Bond-Forming Reactions

3.4 Cycloaddition Reactions

3.5 Metathesis Reactions

3.6 Carbon-Heteroatom Bond-Forming Reactions

3.7 Isomerization Reactions

4 Conclusion

Key words

homogeneous catalysis - organocatalysis - fluorine - solvent effects - additives

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References

1a Povey JF. Smales CM. Hassard SJ. Howard MJ. J. Struct. Biol. 2007, 157: 329

1b Buck M. Q. Rev. Biophys. 1998, 31: 297

2 Eberson L. Hartshorn MP. Perssona O. Radnera F. Chem. Commun. 1996, 2105

3 Bégué J.-P. Bonnet-Delpon D. Crousse B. Synlett 2004, 18

4a Blainey PC. Reid PJ. Spectrochim. Acta, Part A 2001, 57: 2763

4b Juhani M. Kivinen A. Strandman L. Suom. Kemistil. B 1971, 44: 308

5a Reichardt C. Solvents and Solvent Effects in Organic Chemistry Wiley-VCH; Weinheim: 1990.

5b Reichardt C. Chem. Rev. 1994, 94: 2319

6 Freed BK. Biesecker J. Middleton WJ. J. Fluorine Chem. 1990, 48: 63

7 Mock WL. Zhang JZ. Tetrahedron Lett. 1990, 31: 5687

8a Sraïdi K. Dissertation University of Marrakech; Morocco: 1986.

8b Laurence C. Berthelot M. Graton J. In The Chemisty of Phenols Rappoport Z. John Wiley & Sons; Chichester: 2003. p.529

9a Ballinger P. Long FA. J. Am. Chem. Soc. 1960, 82: 795

9b Kirsch P. Modern Fluoroorganic Chemistry Wiley-VCH; Weinheim: 2004.

10 Schadt FL. Bentley TW. Schleyer P.v.R. J. Am. Chem. Soc. 1976, 98: 7667

11 Oh YH. Jang GG. Lim GT. Ryu ZH. Bull. Korean Chem. Soc. 2002, 23: 1089

12 Dyatkin BL. Mochalina EP. Knunyants IL. Tetrahedron 1965, 21: 2991

13 Bentley TW. Carter GE. J. Org. Chem. 1983, 48: 579

14 Kamlet MJ. Abboud JM. Abraham MH. Taft RW. J. Org. Chem. 1983, 48: 2877

15 Stolarova M. Buchtova M. Bekarek V. Acta Univ. Palacki. Olomuc. Fac. Rerum Nat. 1984, 79: 77

16 Spange S. Vilsmeier E. Adolph S. Fährmann A. J. Phys. Org. Chem. 1999, 12: 547

17 Kolling OW. J. Phys. Chem. 1992, 96: 1729

18 Abraham MH. Grellier PL. Prior DV. Morris JJ. Taylor PJ. J. Chem. Soc., Perkin Trans. 2 1990, 521

19a Kivinen A. Murto J. Kilpi L. Suom. Kemistil. B 1967, 40: 336

19b Matesich MA. Knoefel J. Feldman H. Evans DF. J. Phys. Chem. 1973, 77: 366

20 Laurence C. Berthelot M. Helbert M. Sraidi K. J. Phys. Chem. 1989, 93: 3799

21 Lopez DO. Tamarit JL. de la Fuente MR. Perez-Jubindo MA. Salud J. Barriot M. J. Phys. Condens. Matter 2000, 12: 3871

22 MacDonald DD. Dolan B. Heyne JB. J. Solution Chem. 1976, 5: 405

23 Candlin JP. Oldham AR. Discuss. Faraday Soc. 1968, 46: 60

24 Strohmeier W. Grünter K. J. Organomet. Chem. 1975, 90: C45

25 Strohmeier W. Grünter K. J. Organomet. Chem. 1975, 90: C48

26 Teunissen HT. Elsevier CJ. Chem. Commun. 1998, 1367

27 Munshi P. Main AD. Linehan JC. Tai C.-C. Jessop PG. J. Am. Chem. Soc. 2002, 124: 7963

28 Ng SM. Yin C. Yeung CH. Chan TC. Lau CP. Eur. J. Inorg. Chem. 2004, 1788

29 Fache F. Piva O. Synlett 2004, 1294

30 Fache F. Synlett 2004, 2827

31 Burk MJ. Kalberg CS. Pizzano A. J. Am. Chem. Soc. 1998, 120: 4345

32 Cobley CJ. Lennon IC. Praquin C. Zanotti-Gerosa A. Org. Process Res. Dev. 2003, 7: 407

33 Wang Y.-Q. Lu S.-M. Zhou Y.-G. Org. Lett. 2005, 7: 3235

34 Wang Y.-Q. Zhou Y.-G. Synlett 2006, 1189

35 Abe H. Amii H. Uneyama K. Org. Lett. 2001, 3: 313

36 Suzuki A. Mae M. Amii H. Uneyama K. J. Org. Chem. 2004, 69: 5132

37 Dubrovina NV. Tararov VI. Monsees A. Kadyrov R. Fischer C. Börner A. Tetrahedron: Asymmetry 2003, 14: 2739

38 Dubrovina NV. Tararov VI. Monsees A. Spannenberg A. Kostas ID. Börner A. Tetrahedron: Asymmetry 2005, 16: 3640

39 Hsiao Y. Rivera NR. Rosner T. Krska SW. Njolito E. Wang F. Sun Y. Armstrong JD. Grabowski EJJ. Tillye RD. Spindler F. Malan C. J. Am. Chem. Soc. 2004, 126: 9918

40 Zhang W. Zhang X. J. Org. Chem. 2007, 72: 1020

41 Bunlaksananusorn T. Rampf F. Synlett 2005, 17: 2682

42 Neimann K. Neumann R. Org. Lett. 2000, 2: 2861

43a Shryne TM, and Kim L. inventors; (Shell) US Patent 4024165.

43b Kim L. inventors; (Shell) US Patent 4418203.

43c Romanelli MG. inventors; (Exxon) EP 0096130.

44 Ravikumar KS. Barbier F. Bégué J.-P. Bonnet-Delpon D. Tetrahedron 1998, 54: 7457

45 van Vliet MCA. Arends IWCE. Sheldon RA. Chem. Commun. 1999, 821

46 Iskra J. Bonnet-Delpon D. Bégué J.-P. Tetrahedron Lett. 2002, 43: 1001

47 ten Brink G.-J. Fernandes BCM. van Vliet MCA. Arends IWCE. Sheldon RA. J. Chem. Soc., Perkin Trans. 1 2001, 224

48 van Vliet MCA. Arends IWCE. Sheldon RA. Chem. Commun. 1999, 263

49 van Vliet MCA. Arends IWCE. Sheldon RA. Synlett 2001, 1305

50 Legros J. Crousse B. Bonnet-Delpon D. Bégué J.-P. Tetrahedron 2002, 58: 3993

51 Legros J. Crousse B. Bourdon J. Bonnet-Delpon D. Bégué J.-P. Tetrahedron Lett. 2001, 42: 4463

52 Legros J. Crousse B. Bonnet-Delpon D. Bégué J.-P. Eur. J. Org. Chem. 2002, 3290

53 Berkessel A. Adrio JA. Adv. Synth. Catal. 2004, 346: 275

54 Nam W. Oh S.-Y. Sun YJ. Kim J. Kim W.-K. Woo SK. Shin W. J. Org. Chem. 2003, 68: 7903

Kinetic and computational studies on the epoxidation of olefins in HFIP were performed by Berkessel et al.

55a Berkessel A. Adrio JA. J. Am. Chem. Soc. 2006, 128: 13412

55b Berkessel A. Adrio JA. Huettenhain D. Neudoerfl JM. J. Am. Chem. Soc. 2006, 128: 8421

56 Berkessel A. Andreae MRM. Tetrahedron Lett. 2001, 42: 2293

57 Berkessel A. Andreae MRM. Schmickler H. Lex J. Angew. Chem. Int. Ed. 2002, 41: 4481 ; Angew. Chem. 2002, 114, 4461

58 Imada Y. Iida H. Ono S. Masui Y. Murahashi S.-I. Chem. Asian J. 2006, 136

59a Ravikumar KS. Bégué JP. Bonnet-Delpon D. Tetrahedron Lett. 1998, 39: 3141

59b Ravikumar KS. Zhang YM. Bégué JP. Bonnet-Delpon D. Eur. J. Org. Chem. 1998, 2937

60 Fache F. Piva O. Synlett 2002, 2035

61 Fache F. Piva O. Tetrahedron: Asymmetry 2003, 14: 139

62a Annaraj J. Suh Y. Seo MS. Kim SO. Nam W. Chem. Commun. 2005, 4529

62b Park MJ. Lee J. Suh Y. Kim J. Nam W. J. Am. Chem. Soc. 2006, 128: 2630

63 Kawara A. Taguchi T. Tetrahedron Lett. 1994, 35: 8805

64 Kitajima H. Ito K. Katsuki T. Tetrahedron 1997, 53: 17015

65 Kitajima H. Katsuki T. Synlett 1997, 568

66 Evans DA. Rovis T. Kozlowski MC. Tedrow JS. J. Am. Chem. Soc. 1999, 121: 1994

67 Evans DA. Scheidt KA. Johnston JN. Willis MC. J. Am. Chem. Soc. 2001, 123: 4480

68 Zhou J. Tang Y. J. Am. Chem. Soc. 2002, 124: 9030

69 Sibi MP. Chen J. Org. Lett. 2002, 4: 2933

70 Desimoni G. Faita G. Guala M. Laurenti A. Mella M. Chem. Eur. J. 2005, 3816

71 Takita R. Ohshima T. Shibasaki M. Tetrahedron Lett. 2002, 43: 4661

72a Majima K. Takita R. Okada A. Ohshima T. Shibasaki M. J. Am. Chem. Soc. 2003, 125: 15837

72b Park S.-Y. Morimoto H. Matsunaga S. Shibasaki M. Tetrahedron Lett. 2007, 48: 2815

73 Suga H. Kitamura T. Kakehi A. Baba T. Chem. Commun. 2004, 1414

74 Matsukawa S. Mikami K. Tetrahedron: Asymmetry 1995, 6: 2571

75 Tan L. Chen C.-Y. Tillyer RD. Grabowski EJJ. Reider PJ. Angew. Chem. Int. Ed. 1999, 38: 711 ; Angew. Chem. 1999, 111, 724

76 Fuerst DE. Jacobsen EN. J. Am. Chem. Soc. 2005, 127: 8964

77 Willis MC. Piccio VJ.-D. Synlett 2002, 1625

78 Chen S.-H. Hong B.-C. Sua C.-F. Sarshar S. Tetrahedron Lett. 2005, 46: 8899

79 Onitsuka S. Matsuoka Y. Irie R. Katsuki T. Chem. Lett. 2003, 32: 974

80 Marigo M. Kjaersgaard A. Juhl K. Gathergood N. Jorgensen KA. Chem. Eur. J. 2003, 9: 2359

81 Kobayashi S. Kiyohara H. Nakamura Y. Matsubara R. J. Am. Chem. Soc. 2004, 126: 6558

82 Enders D. Voith M. Lenzen A. Angew. Chem. Int. Ed. 2005, 44: 1304 ; Angew. Chem. 2005, 117, 1330

83 Westermann B. Neuhaus C. Angew. Chem. Int. Ed. 2005, 44: 4077 ; Angew. Chem. 2005, 117, 4145

84 Enders D. Vrettou M. Synthesis 2006, 2155

85a Nanda KK. Trotter BW. Tetrahedron Lett. 2005, 46: 2025

85b Jourdan H. Gouhier G. van Hijfte L. Angibaud P. Piettre SR. Tetrahedron Lett. 2005, 46: 8027

86 Nugent WA. McKinney RJ. J. Mol. Catal. 1985, 29: 65

87 Milani B. Anzilutti A. Vicentini L. Sessanta o Santi A. Zangrando E. Geremia S. Mestroni G. Organometallics 1997, 16: 5064

88 Milani B. Corso G. Mestroni G. Carfagna C. Formica M. Seraglia R. Organometallics 2000, 19: 3435

89 Scarel A. Milani B. Zangrando E. Stener M. Furlan S. Fronzoni G. Mestroni G. Gladiali S. Carfagna C. Mosca L. Organometallics 2004, 23: 5593

90 Milani B. Scarel A. Mestroni G. Gladiali S. Taras R. Carfagna C. Mosca L. Organometallics 2002, 21: 1323

91a Scarel A. Durand J. Franchi D. Zangrando E. Mestroni G. Carfagna C. Mosca L. Seraglia R. Consiglio G. Milani B. Chem. Eur. J. 2005, 11: 6014

91b Bergman SD. Goldberg I. Carfagna C. Mosca L. Kol M. Milani B. Organometallics 2006, 25: 6014

92 Scarel A. Durand J. Franchi D. Zangrando E. Mestroni G. Milani B. Gladiali S. Carfagna C. Binotti B. Bronco S. Gragnoli T. J. Organomet. Chem. 2005, 690: 2106

93 Bianchini C. Meli A. Oberhauser W. Segarra AM. Claver C. Suarez EJG. J. Mol. Catal. A: Chem. 2007, 265: 292

94 Koh JH. Larsen AO. Gagne MR. Org. Lett. 2001, 3: 1233

95 Jimenez-Rodriguez C. Eastham GR. Cole-Hamilton DJ. J. Chem. Soc., Dalton Trans. 2005, 1826

96 Mattson AE. Bharadwaj AR. Zuhl AM. Scheidt KA. J. Org. Chem. 2006, 71: 5715

97 Jolly RS. Luedtke G. Sheehan D. Livinghouse T. J. Am. Chem. Soc. 1990, 112: 4965

98 McKinstry L. Livinghouse T. Tetrahedron 1994, 50: 6145

99 O’Mahony DJR. Belanger DB. Livinghouse T. Synlett 1998, 443

100 Heath H. Wolfe B. Livinghouse T. Bae SK. Synthesis 2001, 2341

101 Gilbertson SR. Hoge GS. Genov DG. J. Org. Chem. 1998, 63: 10077

102 Thermal Diels-Alder reaction of sorbates: Boeckman RK. Demko DM. J. Org. Chem. 1982, 47: 1789

103 Saito A. Ono T. Hanzawa Y. J. Org. Chem. 2006, 71: 6437

104 Saito A. Ono T. Takahashi A. Taguchib T. Hanzawa Y. Tetrahedron Lett. 2006, 47: 891

105 Bolm C. Martin M. Simic O. Verrucci M. Org. Lett. 2003, 5: 427

106 Legros J. Crousse B. Ourévitch M. Bonnet-Delpon D. Synlett 2006, 1899

107 Di Salvo A. Spanedda MV. Ourévitch M. Crousse B. Bonnet-Delpon D. Synthesis 2003, 2231

108 Pagenkopf BL. Belanger DB. O’Mahony DJR. Livinghouse T. Synthesis 2000, 1009

109 Patel MC. Livinghouse T. Pagenkopf BL. Org. Synth. 2002, 80: 93

110 Magnus P. Fielding MR. Wells C. Lynch V. Tetrahedron Lett. 2002, 43: 947

111 Wender PA. Croatt MP. Deschamps NM. Angew. Chem. Int. Ed. 2006, 45: 2459 ; Angew. Chem. 2006, 118, 2519

112 Wender PA. Barzilay CM. Dyckman AJ. J. Am. Chem. Soc. 2001, 123: 179

113 Achard M. Tenaglia A. Buono G. Org. Lett. 2005, 12: 2353

114 Cho SY. Lee HI. Cha JK. Org. Lett. 2001, 3: 2891

115 Forman GS. McConnell AE. Tooze RP. van Rensburg WJ. Meyer WH. Kirk MM. Dwyer CL. Serfontein DW. Organometallics 2005, 24: 4528

116 Hong SH. Sanders DP. Lee CW. Grubbs RH. J. Am. Chem. Soc. 2005, 127: 17160

117 Evans DA. Johnson DS. Org. Lett. 1999, 1: 595

118 Ma J.-A. Cahard D. Tetrahedron: Asymmetry 2004, 15: 1007

119 Ma J.-A. Cahard D. J. Fluorine Chem. 2004, 125: 1357

120a Lautens M. Fagnou K. Rovis T. J. Am. Chem. Soc. 2000, 122: 5650

120b Lautens M. Fagnou K. Taylor M. Rovis T. J. Organomet. Chem. 2001, 624: 259

121 Nakano K. Nozaki K. Hiyama T. J. Am. Chem. Soc. 2003, 125: 5501

122 Dohi T. Maruyama A. Minamitsuji Y. Takenaga N. Kita Y. Chem. Commun. 2007, 1224

123a Saito A. Takayama M. Yamazaki A. Numaguchi J. Hanzawa Y. Tetrahedron 2007, 63: 4039

123b Saito A. Numaguchi J. Hanzawa Y. Tetrahedron Lett. 2007, 48: 835

124 Ben-Daniel R. Visser SPd. Shaik S. Neumann R. J. Am. Chem. Soc. 2003, 125: 12116

125 Salvini A. Piacenti F. Frediani P. Devescovi A. Caporali M. J. Organomet. Chem. 2001, 625: 255

126a Kabat MM. Garofalo LM. Daniewski AR. Hutchings SD. Liu W. Okabe M. Radinov R. Zhou Y. J. Org. Chem. 2001, 66: 6141

126b Daniewski AR. Garofalo LM. Hutchings SD. Kabat MM. Liu W. Okabe M. Radinov R. Yiannikouros GP. J. Org. Chem. 2002, 67: 1580

127 Heumann A. Giordano L. Tenaglia A. Tetrahedron Lett. 2003, 44: 1515