1.2 Strategies and Methods in Biocatalysis

A. Díaz-Rodríguez; I. Lavandera

doi:10.1055/sos-SD-214-00071

Share / Bookmark

Facebook Linkedin Weibo

Download PDF

Faber, K. et al.: 2015 Science of Synthesis, 1: Biocatalysis in Organic Synthesis 1 DOI: 10.1055/sos-SD-214-00071

Biocatalysis in Organic Synthesis 1

1.2 Strategies and Methods in Biocatalysis

More Information

Book

Editors: Faber, K.; Fessner, W.-D.; Turner, N. J.

Authors: Asano, Y.; Babich, L.; Bertau, M.; Cobucci-Ponzano, B.; Díaz-Rodríguez, A.; Engel, U.; Faber, K.; Flitsch, S. L.; Glueck, S. M.; Gotor-Fernández, V.; Green, A. P.; Hall, M.; Hartog, A. F.; Hepworth, L. J.; Hollmann, F.; Jeromin, G. E.; Lauchli, R.; Lavandera, I.; Liese, A.; Martínková, L.; Moracci, M.; Pesci, L.; Rodríguez-Mata, M.; Rozzell, D.; Rudat, J.; Schmidberger, J. W.; Servi, S.; Slomka, C.; Syldatk, C.; Tasnádi, G.; Tessaro, D.; Veselá, A. B.; Voglmeir, J.; Wever, R.

Title: Biocatalysis in Organic Synthesis 1

Print ISBN: 9783131741318; Online ISBN: 9783131975218; Book DOI: 10.1055/b-003-125815

1st edition © 2015. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry

Science of Synthesis Reference Libraries

Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

Also available at

Preview
Abstract
Full Text
References
Supplementary Material

Abstract

The use of biocatalysts in organic synthesis and, particularly, in the preparation of optically pure chemicals offers major advantages in terms of selectivity, efficiency, safety, and sustainability. Thus, research groups are becoming more interested in biocatalysis as a tool for challenging synthetic routes. Herein we focus on the different strategies and methods that chemists have designed in order to obtain enantioenriched compounds starting from prochiral or racemic derivatives using enzymes or whole cells as catalysts. In the first part of the chapter, enzymatic desymmetrizations are presented, followed by other established systems dealing with racemates to attain a single or two enantiopure derivatives in the same reaction vessel. Then, the preparation of optically pure compounds in excellent yields and enantiomeric excesses by means of deracemization techniques is discussed. Finally, some recent examples where the combination of enzymes with other (bio)catalysts has provided high-added-value targets are shown.

Key words

desymmetrizations - kinetic resolutions - parallel kinetic resolutions - (cyclic) deracemizations - enantioconvergent processes - dynamic kinetic resolutions - dynamic kinetic asymmetric transformations - concurrent catalysis - cascade reactions - tandem reactions - one-pot reactions - multistep catalysis

1 Wenda S, Illner S, Mell A, Kragl U. Green Chem. 2011; 13: 3007

Search in Google Scholar

2 Bornscheuer UT, Huisman GW, Kazlauskas RJ, Lutz S, Moore JC, Robins K. Nature (London) 2012; 485: 185

Search in Google Scholar

3 Woodley JM, Breuer M, Mink D. Chem. Eng. Res. Des. 2013; 91: 2029

Search in Google Scholar

4 Faber K. Biotransformations in Organic Chemistry. Springer; Berlin 2011

Crossref Search in Google Scholar

5 Behrens GA, Hummel A, Padhi SK, Schätzle S, Bornscheuer UT. Adv. Synth. Catal. 2011; 353: 2191

Search in Google Scholar

6 Davids T, Schmidt M, Boettcher D, Bornscheuer UT. Curr. Opin. Chem. Biol. 2013; 17: 215

PubMed Search in Google Scholar

7 Woodley JM. Curr. Opin. Chem. Biol. 2013; 17: 310

Search in Google Scholar

8 Nestl BM, Nebel BA, Hauer B. Curr. Opin. Chem. Biol. 2011; 15: 187

Search in Google Scholar

9 Muñoz Solano D, Hoyos P, Hernáiz MJ, Alcántara AR, Sánchez-Montero JM. Bioresour. Technol. 2012; 115: 196

PubMed Search in Google Scholar

10 Bjerre J, Rousseau C, Marinescu L, Bols M. Appl. Microbiol. Biotechnol. 2008; 81: 1

Search in Google Scholar

11 Breslow R. J. Biol. Chem. 2009; 284: 1337

PubMed Search in Google Scholar

12 Asymmetric Organic Synthesis with Enzymes. Gotor V, Alfonso I, García-Urdiales E. Wiley-VCH; Weinheim, Germany 2008

Crossref Search in Google Scholar

13 Moss GP. Pure Appl. Chem. 1996; 68: 2193

Crossref Search in Google Scholar

14 Fersht A. Structure and Mechanism in Protein Science. W. H. Freeman; New York 1999

Search in Google Scholar

15 Jacobsen EE, Anthonsen T, Modern Biocatalysis: Stereoselective and Environmentally Friendly Reactions Fessner W.-D, Anthonsen T. Wiley-VCH Weinheim, Germany 2009; 96

16 García-Urdiales E, Alfonso I, Gotor V. Chem. Rev. 2011; 111: PR110

PubMed Search in Google Scholar

17 García-Urdiales E, Lavandera I, Gotor V, Enzyme Catalysis in Organic Synthesis Drauz K, Gröger H, May O. Wiley-VCH Weinheim, Germany 2012; 43

Crossref

18 Cahn RS, Ingold CK, Prelog V. Angew. Chem. 1966; 78: 413 Angew. Chem. Int. Ed. Engl. 1966; 5: 385

Search in Google Scholar

19 Chen C.-S, Fujimoto Y, Girdaukas G, Sih CJ. J. Am. Chem. Soc. 1982; 104: 7294

Crossref Search in Google Scholar

20 Straathof AJJ, Jongejan JA. Enzyme Microb. Technol. 1997; 21: 559

Search in Google Scholar

21 biocatalysis.uni-graz.at/enantio/cgi-bin/enantio.pl (accessed April 2014).

22 Rakels JLL, Straathof AJJ, Hiejnen JJ. Enzyme Microb. Technol. 1993; 15: 1051

PubMed Search in Google Scholar

23 Chen C.-S, Wu S.-H, Girdaukas G, Sih CJ. J. Am. Chem. Soc. 1987; 109: 2812

Crossref Search in Google Scholar

24 Caron G, Kazlauskas RJ. Tetrahedron: Asymmetry 1993; 4: 1995

Crossref Search in Google Scholar

25 Xie Y.-C, Liu H.-Z, Chen J.-Y. Biotechnol. Lett. 1998; 20: 455

Search in Google Scholar

26 Dehli JR, Gotor V. Chem. Soc. Rev. 2002; 31: 365

PubMed Search in Google Scholar

27 Henrot M, Richter MEA, Maddaluno J, Hertweck C, De Paolis M. Angew. Chem. 2012; 124: 9725 Angew. Chem. Int. Ed. 2012; 51: 9587

PubMed Search in Google Scholar

28 Berezina N, Kozma E, Furstoss R, Alphand V. Adv. Synth. Catal. 2007; 349: 2049

Search in Google Scholar

29 Fink MJ, Fischer TC, Rudroff F, Dudek H, Fraaije MW, Mihovilovic MD. J. Mol. Catal. B: Enzym. 2011; 73: 9

Search in Google Scholar

30 Martínez-Montero S, Fernández S, Sanghvi YS, Gotor V, Ferrero M. J. Org. Chem. 2010; 75: 6605

PubMed Search in Google Scholar

31 Dehli JR, Gotor V. J. Org. Chem. 2002; 67: 1716

PubMed Search in Google Scholar

32 Bianchi P, Roda G, Riva S, Danieli B, Zabelinskaja-Mackova A, Griengl H. Tetrahedron 2001; 57: 2213

Search in Google Scholar

33 Dehli JR, Gotor V. ARKIVOC 2002; 196

34 Faber K. Chem.–Eur. J. 2001; 7: 5005

Search in Google Scholar

35 Gruber CC, Lavandera I, Faber K, Kroutil W. Adv. Synth. Catal. 2006; 348: 1789

Crossref Search in Google Scholar

36 Voss CV, Gruber CC, Kroutil W. Synlett 2010; 991

37 Rachwalski M, Vermue N, Rutjes FPJT. Chem. Soc. Rev. 2013; 42: 9268

PubMed Search in Google Scholar

38 Soda K, Oikawa T, Yokoigawa K. J. Mol. Catal. B: Enzym. 2001; 11: 149

Crossref Search in Google Scholar

39 Voss CV, Gruber CC, Faber K, Knaus T, Macheroux P, Kroutil W. J. Am. Chem. Soc. 2008; 130: 13969

PubMed Search in Google Scholar

40 Kato D, Mitsuda S, Ohta H. J. Org. Chem. 2003; 68: 7234

PubMed Search in Google Scholar

41 Shin G, Mathew S, Shon M, Kim B.-G, Yun H. Chem. Commun. (Cambridge) 2013; 49: 8629

PubMed Search in Google Scholar

42 Köhler V, Wilson YM, Dürrenberger M, Ghislieri D, Churakova E, Quinto T, Knörr L, Häussinger D, Hollmann F, Turner NJ, Ward TR. Nat. Chem. 2013; 5: 93

PubMed Search in Google Scholar

43 Turner NJ. Chem. Rev. 2011; 111: 4073

PubMed Search in Google Scholar

44 Turner NJ, Enzyme Catalysis in Organic Synthesis Drauz K, Gröger H, May O. Wiley-VCH Weinheim, Germany 2012; 1535

Crossref

45 Kroutil W, Faber K. Tetrahedron: Asymmetry 1998; 9: 2901

Crossref Search in Google Scholar

46 Strauss UT, Felfer U, Faber K. Tetrahedron: Asymmetry 1999; 10: 107

Crossref Search in Google Scholar

47 Biade AE, Bourdillon C, Laval JM, Mairesse G, Moiroux J. J. Am. Chem. Soc. 1992; 114: 893

Search in Google Scholar

48 Oikawa T, Mukoyama S, Soda K. Biotechnol. Bioeng. 2001; 73: 80

PubMed Search in Google Scholar

49 Wallner SR, Pogorevc M, Trauthwein H, Faber K. Eng. Life Sci. 2004; 4: 512

Search in Google Scholar

50 Kroutil W, Mischitz M, Faber K. J. Chem. Soc., Perkin Trans. 1 1997; 3629

51 Pedragosa-Moreau S, Archelas A, Furstoss R. J. Org. Chem. 1993; 58: 5533

Crossref Search in Google Scholar

52 Schober M, Toesch M, Knaus T, Strohmeier GA, van Loo B, Fuchs M, Hollfelder F, Macheroux P, Faber K. Angew. Chem. 2013; 125: 3359 Angew. Chem. Int. Ed. 2013; 52: 3277

PubMed Search in Google Scholar

53 Takano S, Suzuki M, Ogasawara K. Tetrahedron: Asymmetry 1993; 4: 1043

Search in Google Scholar

54 Lemke K, Ballschuh S, Kunath A, Theil F. Tetrahedron: Asymmetry 1997; 8: 2051

Search in Google Scholar

55 Gadler P, Faber K. Trends Biotechnol. 2007; 25: 83

PubMed Search in Google Scholar

56 Schober M, Knaus T, Toesch M, Macheroux P, Wagner U, Faber K. Adv. Synth. Catal. 2012; 354: 1737

Search in Google Scholar

57 Szymański W, Westerbeek A, Janssen DB, Feringa BL. Angew. Chem. 2011; 123: 10900 Angew. Chem. Int. Ed. 2011; 50: 10712

PubMed Search in Google Scholar

58 Lee JH, Han K, Kim M.-J, Park J. Eur. J. Org. Chem. 2010; 999

59 Pellissier H. Tetrahedron 2011; 67: 3769

Crossref Search in Google Scholar

60 Kim Y, Park J, Kim M.-J. ChemCatChem 2011; 3: 271

Crossref Search in Google Scholar

61 Hussain I, Bäckvall J.-E, Enzyme Catalysis in Organic Synthesis Drauz K, Gröger H, May O. Wiley-VCH Weinheim, Germany 2012; 1777

Crossref

62 Tan DS, Günter MM, Drueckhammer DG. J. Am. Chem. Soc. 1995; 117: 9093

Crossref Search in Google Scholar

63 Ebbers EJ, Ariaans GJA, Houbiers JPM, Bruggink A, Zwanenburg B. Tetrahedron 1997; 53: 9417

Crossref Search in Google Scholar

64 Asano Y, Hölsch K, Enzyme Catalysis in Organic Synthesis Drauz K, Gröger H, May O. Wiley-VCH Weinheim, Germany 2012; 1607

Crossref

65 Schichl DA, Enthaler S, Holla W, Riermeier T, Kragl U, Beller M. Eur. J. Org. Chem. 2008; 3506

66 El Blidi L, Nechab M, Vanthuyne N, Gastaldi S, Bertrand MP, Gil G. J. Org. Chem. 2009; 74: 2901

PubMed Search in Google Scholar

67 Vongvilai P, Larsson R, Ramström O. Adv. Synth. Catal. 2008; 350: 448

Crossref Search in Google Scholar

68 Vongvilai P, Ramström O. J. Am. Chem. Soc. 2009; 131: 14419

PubMed Search in Google Scholar

69 van der Deen H, Cuiper AD, Hof RP, van Oeveren A, Feringa BL, Kellogg RM. J. Am. Chem. Soc. 1996; 118: 3801

Crossref Search in Google Scholar

70 Thuring JWJF, Klunder AJH, Nefkens GHL, Wegman MA, Zwanenburg B. Tetrahedron Lett. 1996; 37: 4759

Crossref Search in Google Scholar

71 Sharfuddin M, Narumi A, Iwai Y, Miyazawa K, Yamada S, Kakuchi T, Kaga H. Tetrahedron: Asymmetry 2003; 14: 1581

Crossref Search in Google Scholar

72 Lozano P, De Diego T, Mira C, Montague K, Vaultier M, Iborra JL. Green Chem. 2009; 11: 538

Crossref Search in Google Scholar

73 Cuetos A, Rioz-Martínez A, Bisogno FR, Grischek B, Lavandera I, de Gonzalo G, Kroutil W, Gotor V. Adv. Synth. Catal. 2012; 354: 1749

Search in Google Scholar

74 Rioz-Martínez A, Cuetos A, Rodríguez C, de Gonzalo G, Lavandera I, Fraaije MW, Gotor V. Angew. Chem. 2011; 123: 8537 Angew. Chem. Int. Ed. 2011; 50: 8387

PubMed Search in Google Scholar

75 Cuetos A, Lavandera I, Gotor V. Chem. Commun. (Cambridge) 2013; 49: 10688

PubMed Search in Google Scholar

76 Shvo Y, Czarkie D, Rahamim Y, Chodosh DF. J. Am. Chem. Soc. 1986; 108: 7400

Search in Google Scholar

77 Trost BM, Bunt RC, Lemoine RC, Calkins TL. J. Am. Chem. Soc. 2000; 122: 5968

Crossref Search in Google Scholar

78 Steinreiber J, Faber K, Griengl H. Chem.–Eur. J. 2008; 14: 8060

Crossref PubMed Search in Google Scholar

79 Martín-Matute B, Edin M, Bäckvall J.-E. Chem.–Eur. J. 2006; 12: 6053

Crossref PubMed Search in Google Scholar

80 Borén L, Leijondahl K, Bäckvall J.-E. Tetrahedron Lett. 2009; 50: 3237

Crossref Search in Google Scholar

81 Krumlinde P, Bogár K, Bäckvall J.-E. Chem.–Eur. J. 2010; 16: 4031

Crossref PubMed Search in Google Scholar

82 Steinreiber J, Schürmann M, Wolberg M, van Assema F, Reisinger C, Fesko K, Mink D, Griengl H. Angew. Chem. 2007; 119: 1648 Angew. Chem. Int. Ed. 2007; 46: 1624

PubMed Search in Google Scholar

83 Steinreiber J, Schürmann M, van Assema F, Wolberg M, Fesko K, Reisinger C, Mink D, Griengl H. Adv. Synth. Catal. 2007; 349: 1379

Crossref Search in Google Scholar

84 Enzyme Catalysis in Organic Synthesis. Drauz K, Gröger H, May O. Wiley-VCH; Weinheim, Germany 2012

Crossref Search in Google Scholar

85 Tietze LF, Brasche G, Gericke KM. Domino Reactions in Organic Synthesis. Wiley-VCH; Weinheim, Germany 2006

Crossref Search in Google Scholar

86 Bruggink A, Schoevaart R, Kieboom T. Org. Process Res. Dev. 2003; 7: 622

Search in Google Scholar

87 Pellissier H. Tetrahedron 2013; 69: 7171

Crossref Search in Google Scholar

88 Ricca E, Brucher B, Schrittwieser JH. Adv. Synth. Catal. 2011; 353: 2239

Search in Google Scholar

89 Vaxelaire C, Winter P, Christmann M. Angew. Chem. 2011; 123: 3685 Angew. Chem. Int. Ed. 2011; 50: 3605

PubMed Search in Google Scholar

90 Trost BM. Science (Washington, D. C.) 1991; 254: 1471

PubMed Search in Google Scholar

91 Burns NZ, Baran PS, Hoffmann RW. Angew. Chem. 2009; 121: 2896 Angew. Chem. Int. Ed. 2009; 48: 2854

PubMed Search in Google Scholar

92 Clarke PA, Santos S, Martin WHC. Green Chem. 2007; 9: 438

Search in Google Scholar

93 Hayashi Y, Umemiya S. Angew. Chem. 2013; 125: 3435 Angew. Chem. Int. Ed. 2013; 52: 3450

PubMed Search in Google Scholar

94 Green Chemistry: Designing Chemistry for the Environment. Anastas PT, Williamson TC. Oxford University Press; Oxford 1998

Search in Google Scholar

95 Anastas P, Eghbali N. Chem. Soc. Rev. 2010; 39: 301

PubMed Search in Google Scholar

96 Sheldon RA, Multi-Step Enzyme Catalysis: Biotransformations and Chemoenzymatic Synthesis García-Junceda E. Wiley-VCH Weinheim, Germany 2008; 109

Crossref

97 Lopez-Gallego F, Schmidt-Dannert C. Curr. Opin. Chem. Biol. 2010; 14: 174

PubMed Search in Google Scholar

98 Schrittwieser JH, Sattler J, Resch V, Mutti FG, Kroutil W. Curr. Opin. Chem. Biol. 2011; 15: 249

PubMed Search in Google Scholar

99 Bisogno FR, Lavandera I, Gotor V. Kirk-Othmer Encyclopedia of Chemical Technology Wiley Hoboken, NJ 2011; 1

100 Oroz-Guinea I, García-Junceda E. Curr. Opin. Chem. Biol. 2013; 17: 236

PubMed Search in Google Scholar

101 Hollmann F, Arends IWCE, Buehler K. ChemCatChem 2010; 2: 762

Search in Google Scholar

102 Rodríguez C, Lavandera I, Gotor V. Curr. Org. Chem. 2012; 16: 2525

Search in Google Scholar

103 Aksu S, Arends IWCE, Hollmann F. Adv. Synth. Catal. 2009; 351: 1211

Crossref Search in Google Scholar

104 Ferrandi EE, Monti D, Patel I, Kittl R, Haltrich D, Riva S, Ludwig R. Adv. Synth. Catal. 2012; 354: 2821

Search in Google Scholar

105 Könst P, Kara S, Kochius S, Holtmann D, Arends IWCE, Ludwig R, Hollmann F. ChemCatChem 2013; 5: 3027

Crossref Search in Google Scholar

106 Voss CV, Gruber CC, Kroutil W. Angew. Chem. 2008; 120: 753 Angew. Chem. Int. Ed. 2008; 47: 741

PubMed Search in Google Scholar

107 Gruber CC, Nestl BM, Gross J, Hildebrandt P, Bornscheuer UT, Faber K, Kroutil W. Chem.–Eur. J. 2007; 13: 8271

PubMed Search in Google Scholar

108 Monti D, Ferrandi EE, Zanellato I, Hua L, Polentini F, Carrea G, Riva S. Adv. Synth. Catal. 2009; 351: 1303

Search in Google Scholar

109 Simon RC, Richter N, Busto E, Kroutil W. ACS Catal. 2014; 4: 129

Crossref Search in Google Scholar

110 Koszelewski D, Grischek B, Glueck SM, Kroutil W, Faber K. Chem.–Eur. J. 2011; 17: 378

PubMed Search in Google Scholar

111 Koszelewski D, Pressnitz D, Clay D, Kroutil W. Org. Lett. 2009; 11: 4810

PubMed Search in Google Scholar

112 Koszelewski D, Müller N, Schrittwieser JH, Faber K, Kroutil W. J. Mol. Catal. B: Enzym. 2010; 63: 39

Crossref Search in Google Scholar

113 Fuchs M, Tauber K, Sattler J, Lechner H, Pfeffer J, Kroutil W, Faber K. RSC Adv. 2012; 2: 6262

Crossref Search in Google Scholar

114 Sattler JH, Fuchs M, Tauber K, Mutti FG, Faber K, Pfeffer J, Haas T, Kroutil W. Angew. Chem. 2012; 124: 9290 Angew. Chem. Int. Ed. 2012; 51: 9156

PubMed Search in Google Scholar

115 Simon RC, Grischek B, Zepeck F, Steinreiber A, Belaj F, Kroutil W. Angew. Chem. 2012; 124: 6817 Angew. Chem. Int. Ed. 2012; 51: 6713

PubMed Search in Google Scholar

116 Schrittwieser JH, Lavandera I, Seisser B, Mautner B, Lutje Spelberg JH, Kroutil W. Tetrahedron: Asymmetry 2009; 20: 483

Crossref Search in Google Scholar

117 Schrittwieser JH, Lavandera I, Seisser B, Mautner B, Kroutil W. Eur. J. Org. Chem. 2009; 2293

118 Ma SK, Gruber J, Davis C, Newman L, Gray D, Wang A, Grate J, Huisman GW, Sheldon RA. Green Chem. 2010; 12: 81

Search in Google Scholar

119 Szymanski W, Postema CP, Tarabiono C, Berthiol F, Campbell-Verduyn L, de Wildeman S, de Vries JG, Feringa BL, Janssen DB. Adv. Synth. Catal. 2010; 352: 2111

Search in Google Scholar

120 Wu S, Chen Y, Xu Y, Li A, Xu Q, Glieder A, Li Z. ACS Catal. 2014; 4: 409

Crossref Search in Google Scholar

121 Di Gennaro P, Kazandjian LV, Mezzetti F, Sello G. Arch. Microbiol. 2013; 195: 269

PubMed Search in Google Scholar

122 Schrewe M, Ladkau N, Bühler B, Schmid A. Adv. Synth. Catal. 2013; 355: 1693

Crossref Search in Google Scholar

123 Peters RJRW, Marguet M, Marais S, Fraaije MW, van Hest JCM, Lecommandoux S. Angew. Chem. 2014; 126: 150 Angew. Chem. Int. Ed. 2014; 53: 146

Search in Google Scholar

124 Denard CA, Hartwig JF, Zhao H. ACS Catal. 2013; 3: 2856

Crossref Search in Google Scholar

125 Hollmann F, Lin P.-C, Witholt B, Schmid A. J. Am. Chem. Soc. 2003; 125: 8209

PubMed Search in Google Scholar

126 Quinto T, Köhler V, Ward TR. Top. Catal. 2014; 57: 321

Search in Google Scholar

127 Hildebrand F, Lütz S. Chem.–Eur. J. 2009; 15: 4998

PubMed Search in Google Scholar

128 Poizat M, Arends IWCE, Hollmann F. J. Mol. Catal. B: Enzym. 2010; 63: 149

Search in Google Scholar

129 Lutz J, Hollmann F, Ho TV, Schnyder A, Fish RH, Schmid A. J. Organomet. Chem. 2004; 689: 4783

Search in Google Scholar

130 Höllrigl V, Otto K, Schmid A. Adv. Synth. Catal. 2007; 349: 1337

Search in Google Scholar

131 Hildebrand F, Lütz S. Tetrahedron: Asymmetry 2007; 18: 1187

Search in Google Scholar

132 Burda E, Hummel W, Gröger H. Angew. Chem. 2008; 120: 9693 Angew. Chem. Int. Ed. 2008; 47: 9551

PubMed Search in Google Scholar

133 Gauchot V, Kroutil W, Schmitzer AR. Chem.–Eur. J. 2010; 16: 6748

PubMed Search in Google Scholar

134 Kanbak-Aksu S, Hasan MN, Hagen WR, Hollmann F, Sordi D, Sheldon RA, Arends IWCE. Chem. Commun. (Cambridge) 2012; 48: 5745

PubMed Search in Google Scholar

135 Filice M, Marciello M, del Puerto Morales M, Palomo JM. Chem. Commun. (Cambridge) 2013; 49: 6876

PubMed Search in Google Scholar

136 Tenbrink K, Seßler M, Schatz J, Gröger H. Adv. Synth. Catal. 2011; 353: 2363

Search in Google Scholar

137 Denard CA, Huang H, Bartlett MJ, Lu L, Tan Y, Zhao H, Hartwig JF. Angew. Chem. 2014; 126: 475 Angew. Chem. Int. Ed. 2014; 53: 465

PubMed Search in Google Scholar

138 Wang ZJ, Clary KN, Bergman RG, Raymond KN, Toste FD. Nat. Chem. 2013; 5: 100

PubMed Search in Google Scholar

139 Hanefeld U, Gardossi L, Magner E. Chem. Soc. Rev. 2009; 38: 453

PubMed Search in Google Scholar

140 Engström K, Johnston EV, Verho O, Gustafson KPJ, Shakeri M, Tai C.-W, Bäckvall J.-E. Angew. Chem. 2013; 125: 14256 Angew. Chem. Int. Ed. 2013; 52: 14006

PubMed Search in Google Scholar

141 Ward TR. Acc. Chem. Res. 2011; 44: 47

PubMed Search in Google Scholar

142 Hyster TK, Knörr L, Ward TR, Rovis T. Science (Washington, D. C.) 2012; 338: 500

PubMed Search in Google Scholar

143 Foulkes JM, Malone KJ, Coker VS, Turner NJ, Lloyd JR. ACS Catal. 2011; 1: 1589

Search in Google Scholar

144 Baer K, Kraußer M, Burda E, Hummel W, Berkessel A, Gröger H. Angew. Chem. 2009; 121: 9519 Angew. Chem. Int. Ed. 2009; 48: 9355

PubMed Search in Google Scholar

145 Sonoike S, Itakura T, Kitamura M, Aoki S. Chem.–Asian J. 2012; 7: 64

PubMed Search in Google Scholar