Synthesis 2015; 47(06): 760-768
DOI: 10.1055/s-0034-1379733
short review
© Georg Thieme Verlag Stuttgart · New York

Popular Synthetic Approaches To Pharmaceuticals

David J. Ager*
DSM ChemTech R&D BV, PMB 150, 9650 Strickland Road Suite 103, Raleigh, NC 27615, USA   Email: david.ager@dsm.com
› Author Affiliations
Further Information

Publication History

Received: 01 July 2014

Accepted after revision: 24 November 2014

Publication Date:
22 December 2014 (online)


Abstract

The pharmaceutical industry continues to look at the use of ‘green’ methods, including those that allow for shorter synthetic sequences. The use of biocatalysis continues to grow, including transformations that are difficult to perform by standard chemical means. Flow reactions are also growing in popularity, as the equipment becomes available at all scales. The use of flow techniques also allows for the use of high temperatures and pressures, as well as the preparation of hazardous intermediates and use of hazardous reagents, as inventories of these dangerous materials can be kept to a minimum. New reagents and reactions continue to be developed to improve important bond-forming reactions and to allow new types of reactivity, which can be exploited to provide shorter and more efficient reaction pathways.

1 Introduction

2 Green Chemistry

2.1 Biocatalytic Methods

2.2 Flow Chemistry

3 Bond-Forming Reactions

3.1 Aryl-Coupling Reactions

3.2 C–H Bond Activation

3.3 Alcohol Substitutions

3.4 Ammonolysis and Amide Bond Formation

4 Reactions In/On Water

5 Reductions

5.1 Amide Reductions

6 Summary

 
  • References

  • 1 Roughley SD, Jordan AM. J. Med. Chem. 2011; 54: 3451
  • 2 Carey JS, Laffan D, Thomson C, Williams MT. Org. Biomol. Chem. 2006; 4: 2337
  • 3 Farina V, Reeves JT, Senanayake CH, Song JJ. Chem. Rev. 2006; 106: 2734
    • 4a Sheldon RA. Green Chem. 2007; 9: 1273
    • 4b Keith LH, Gron LU, Young JL. Chem. Rev. 2007; 107: 2695
    • 4c Li C.-J, Trost BM. Proc. Natl. Acad. Sci. U.S.A. 2008; 105: 13197
    • 4d Kang E. Tetrahedron 2010; 66: 1029
    • 4e Watson WJ. W. Green Chem. 2012; 14: 251
    • 4f Jiménez-González C, Constable DJ. C, Ponder CS. Chem. Soc. Rev. 2012; 41: 1485
    • 4g Dunn PJ. Chem. Soc. Rev. 2012; 41: 1452
    • 4h Sheldon RA. Chem. Soc. Rev. 2012; 41: 1437
    • 4i Kjell DP, Watson IA, Wolfe CN, Spitler JT. Org. Process Res. Dev. 2013; 17: 169
    • 4j Leahy DK, Tucker JL, Mergelsberg I, Dunn PJ, Kopach ME, Purohit VC. Org. Process Res. Dev. 2013; 17: 1099
  • 5 Jiménez-González C, Ollech C, Pyrz W, Hughes D, Broxterman QB, Bhathela N. Org. Process Res. Dev. 2013; 17: 239
  • 6 Sheldon RA. Chem. Commun. 2008; 3352
  • 7 Bryan MC, Dillon B, Hamann LG, Hughes GJ, Kopach ME, Peterson EA, Pourashraf M, Raheem I, Richardson P, Richter D, Sneddon HF. J. Med. Chem. 2013; 56: 6007
  • 8 Ho SV, McLaughlin JM, Cue BW, Dunn PJ. Green Chem. 2010; 12: 755
    • 9a Mason BP, Price KE, Steinbacher JL, Bogdan AR, McQuade DT. Chem. Rev. 2007; 107: 2300
    • 9b Proctor L, Dunn PJ, Hawkins JM, Wells AS, Williams MT. Continuous Processing in the Pharmaceutical Industry . In Green Chemistry in the Pharmaceutical Industry . Dunn PJ, Wells AS, Williams MT. Wiley-VCH; Weinheim: 2010: 221
    • 10a Walsh PJ, Li H, de Parrodi CA. Chem. Rev. 2007; 107: 2503
    • 10b de Cienfuegos LA, Robles R, Miguel D, Justica J, Cuerva JM. ChemSusChem 2011; 4: 1035
    • 11a McGinagle FI, MacMillan DS, Murray J, Sneddon HF, Jamieson C, Watson AJ. B. Green Chem. 2013; 15: 1159
    • 11b Adams JP, Alder CM, Andrews I, Bullion AM, Campbell-Crawford M, Darcy MG, Hayler JD, Henderson RK, Oare CA, Pendrak I, Redman AM, Shuster LE, Sneddon HF, Walker MD. Green Chem. 2013; 15: 1542
  • 12 Wender PA, Verma VA, Paxton TJ, Pillow TH. Acc. Chem. Res. 2008; 41: 40
    • 13a Clouthier CM, Pelletier JN. Chem. Soc. Rev. 2012; 41: 1585
    • 13b Wells AS, Finch GL, Michels PC, Wong JW. Org. Process Res. Dev. 2012; 16: 1986
    • 14a Martín-Matute B, Edin M, Bäckvall J.-E. Chem. Eur. J. 2006; 12: 6053
    • 14b Fransson A.-BL, Xu Y, Leijondahl K, Bäckvall J.-E. J. Org. Chem. 2006; 71: 6309
    • 14c Strübing D, Krumlinde P, Piera J, Bäckvall J.-E. Adv. Synth. Catal. 2007; 349: 1577
    • 14d Choi JH, Choi YK, Kim YH, Park ES, Kim EJ, Kim M.-J, Park J. J. Org. Chem. 2004; 69: 1972
    • 14e Akai S, Tanimoto K, Kanao Y, Egi M, Yamamoto T, Kita Y. Angew. Chem. Int. Ed. 2006; 45: 2592
    • 14f Dijksman A, Elzinga JM, Li Y.-X, Arends IW. C. E, Sheldon RA. Tetrahedron: Asymmetry 2002; 13: 879
    • 14g Kim M.-J, Chung YI, Choi YK, Lee HK, Kim D, Park J. J. Am. Chem. Soc. 2003; 125: 11494
    • 14h Berkessel A, Sebastian-Ibarz ML, Müller TN. Angew. Chem. Int. Ed. 2006; 45: 6567
    • 14i van As BA. C, van Buijtenen J, Heise A, Broxterman QB, Verzijl GK. M, Palmans AR. A, Meijer EW. J. Am. Chem. Soc. 2005; 127: 9964
    • 15a Paetzold J, Bäckvall J.-E. J. Am. Chem. Soc. 2005; 127: 17620
    • 15b Parvulescu AN, Jacobs PA, De Vos DE. Chem. Eur. J. 2007; 13: 2034
    • 15c Han K, Park J, Kim M.-J. J. Org. Chem. 2008; 73: 4302
    • 15d Gastaldi S, Escoubet S, Vanthuyne N, Gil G, Bertrand MP. Org. Lett. 2007; 9: 837
    • 15e Kim M.-J, Kim W.-H, Han K, Choi YK, Park J. Org. Lett. 2007; 9: 1157
  • 16 Thalén LK, Zhao D, Sortais J.-B, Paetzold J, Hoben C, Bäckvall J.-E. Chem. Eur. J. 2009; 15: 3403
  • 17 Baxter S, Royer S, Grogan G, Brown F, Holt-Tiffin KE, Taylor IN, Fotheringham IG, Campopiano DJ. J. Am. Chem. Soc. 2012; 134: 19310
    • 18a Chenault HK, Dahmer J, Whitesides GM. J. Am. Chem. Soc. 1989; 111: 6354
    • 18b Hsu S.-K, Lo H.-H, Kao C.-H, Lee D.-S, Hsu W.-H. Biotechnol. Prog. 2006; 22: 1578
  • 19 May O, Verseck S, Bommarius A, Drauz K. Org. Process Res. Dev. 2002; 6: 452
    • 20a Ishikawa T, Mukohara Y, Watabe K, Kobayashi S, Nakamura H. Biosci. Biotechnol. Biochem. 1994; 58: 265
    • 20b Wagner T, Hantke B, Wagner F. J. Biotechnol. 1996; 46: 63
    • 20c May O, Siemann M, Pietzsch M, Kiess M, Mattes R, Syldatk C. J. Biotechnol. 1998; 61: 1
    • 21a Tokuyama S. J. Mol. Catal. B: Enzym. 2001; 12: 3
    • 21b Wilms B, Wiese A, Syldatk C, Mattes R, Altenbuchner J. J. Biotechnol. 2001; 86: 19
    • 21c Nozaki H, Takenaka Y, Kira I, Watanabe K, Yokozeki K. J. Mol. Catal. B: Enzym. 2005; 32: 213
    • 22a Ni Y, Xu J.-H. Biotechnol. Adv. 2012; 30: 1279
    • 22b Huisman GW, Liang J, Krebber A. Curr. Opin. Chem. Biol. 2010; 14: 122
    • 22c Panke S, Wubbolts M. Curr. Opin. Chem. Biol. 2005; 9: 188
    • 22d de Wildeman SM. A, Sonke T, Schoemaker HE, May O. Acc. Chem. Res. 2007; 40: 1260
    • 22e Calvin SJ, Mangan D, Miskelly I, Moody TS, Stevenson PJ. Org. Process Res. Dev. 2012; 16: 82
  • 23 Matsuda T, Yamanaka R, Nakamura K. Tetrahedron: Asymmetry 2009; 20: 513
    • 24a Chen Y, Goldberg SL, Hanson RL, Parker WL, Gill I, Tully TP, Montana MA, Goswami A, Patel RN. Org. Process Res. Dev. 2011; 15: 241
    • 24b Höhne M, Bornscheuer UT. ChemCatChem 2009; 1: 42
    • 24c Roengpithya C, Patterson DA, Livingston AG, Taylor PC, Irwin JL, Parrett MR. Chem. Commun. 2007; 3462
    • 24d Abrahamson MJ, Vázquez-Figueroa E, Woodall NB, Moore JC, Bommarius AS. Angew. Chem. Int. Ed. 2012; 51: 3969
    • 25a Ohno M, Otsuka M. Org. React. 1989; 37: 1
    • 25b Zhu L.-M, Tedford MC. Tetrahedron 1990; 46: 6587
  • 26 Hermann M, Kietzmann MU, Ivančić M, Zenzmaier C, Luiten RG. M, Skranc W, Wubbolts M, Winkler M, Birner-Gruenberger R, Pichler H, Schwab H. J. Biotechnol. 2008; 133: 301
  • 27 Balke K, Kadow M, Mallin H, Saß S, Bornscheuer UT. Org. Biomol. Chem. 2012; 10: 6249
  • 28 Kayser MM. Tetrahedron 2009; 65: 947
  • 29 Rao NN, Lütz S, Würges K, Minör D. Org. Process Res. Dev. 2009; 13: 607
  • 30 Coelho PS, Brustad EM, Kannan A, Arnold FH. Science (Washington, D.C.) 2013; 339: 307
    • 31a Watts P, Wiles C. Org. Biomol. Chem. 2007; 5: 727
    • 31b Roberge DM, Zimmerman B, Rainone F, Gottsponer M, Eyholzer M, Kockmann N. Org. Process Res. Dev. 2008; 12: 905
    • 31c Kashid MN, Kiwi-Minsker L. Ind. Eng. Chem. Res. 2009; 48: 6465
    • 31d Hessel V, Gürsel IV, Wang Q, Noël T, Lang J. Chem. Eng. Technol. 2012; 35: 1184
    • 31e Anderson NG. Org. Process Res. Dev. 2012; 16: 852
    • 31f Poechlauer P, Manley J, Broxterman R, Gregertsen B, Ridemark M. Org. Process Res. Dev. 2012; 16: 1586
  • 32 Illg T, Löb P, Hessel V. Bioorg. Med. Chem. 2010; 18: 3707
  • 33 Benali O, Deal M, Farrant E, Tapolczay DJ, Wheeler R. Org. Process Res. Dev. 2008; 12: 1007
  • 34 Knudsen KR, Holden J, Ley SV, Ladlow M. Adv. Synth. Catal. 2007; 349: 535
    • 35a Griffiths-Jones CM, Hopkin MD, Jönsson D, Ley SV, Tapolczay DJ, Vickerstaffe E, Ladlow M. J. Comb. Chem. 2007; 9: 422
    • 35b Baumann M, Baxendale IR, Kuratli C, Ley SV, Martin RE, Schneider J. ACS Comb. Sci. 2011; 13: 405
    • 36a Sahoo HR, Kralj JG, Jensen KF. Angew. Chem. Int. Ed. 2007; 46: 5704
    • 36b Wiles C, Watts P. Org. Process Res. Dev. 2008; 12: 1001
  • 37 Brodmann T, Koos P, Metzger A, Knochel P, Ley SV. Org. Process Res. Dev. 2012; 16: 1102
  • 38 Carter CF, Lange H, Ley SV, Baxendale IR, Wittkamp B, Goode JG, Gaunt NL. Org. Process Res. Dev. 2010; 14: 393
  • 39 Cervera-Padrell AE, Nielsen JP, Pedersen MJ, Christensen KM, Mortensen AR, Skovby T, Dam-Johansen K, Kiil S, Gernaey KV. Org. Process Res. Dev. 2012; 16: 901
    • 40a Browne DL, Wright S, Deadman DJ, Dunnage S, Baxendale IR, Turner RM, Ley SV. Rapid Commun. Mass Spectrom. 2012; 26: 1999
    • 40b Foley DA, Doecke CW, Buser JY, Merritt JM, Murphy L, Kissane M, Collins SG, Maguire AR, Kaerner A. J. Org. Chem. 2011; 76: 9630
    • 40c Dalitz F, Maiwald M, Guthausen G. Chem. Eng. Sci. 2012; 75: 318
    • 40d Mozharov S, Nordon A, Girkin JM, Littlejohn D. Lab Chip 2010; 10: 2101
  • 41 Mascia S, Heider PL, Zhang H, Lakerveld R, Benyahia B, Barton PI, Braatz RD, Cooney CL, Evans JM. B, Jamison TF, Jensen KF, Myerson AS, Trout BL. Angew. Chem. Int. Ed. 2013; 52: 12359
    • 42a Usutani H, Tomida Y, Nagaki A, Okamoto H, Nokami T, Yoshida J.-i. J. Am. Chem. Soc. 2007; 129: 3046
    • 42b Yoshida J.-i, Takahashi Y, Nagaki A. Chem. Commun. 2013; 49: 9896
  • 43 Nagaki A, Kim H, Yoshida J.-i. Angew. Chem. Int. Ed. 2008; 47: 7833
  • 44 Hampton PD, Whealon MD, Roberts LM, Yaeger AA, Boysdon R. Org. Process Res. Dev. 2008; 12: 946
    • 45a McConnell JR, Hitt JE, Daugs ED, Rey TA. Org. Process Res. Dev. 2008; 12: 940
    • 45b van der Linden JJ. M, Hilberink PW, Kronenburg CM. P, Kemperman GJ. Org. Process Res. Dev. 2008; 12: 911
    • 46a Roydhouse MD, Ghaini A, Constantinou A, Cantu-Perez A, Motherwell WB, Gavriilidis A. Org. Process Res. Dev. 2011; 15: 989
    • 46b Irfan M, Glasnov TN, Kappe CO. Org. Lett. 2011; 13: 984
    • 46c Allian AD, Richter SM, Kallemeyn JM, Robbins TA, Kishore V. Org. Process Res. Dev. 2011; 15: 91
  • 47 Chambers RD, Sandford G, Trmcic J, Okazoe T. Org. Process Res. Dev. 2008; 12: 339
    • 48a Kulkarni AA, Nivangune NT, Kalyani VS, Joshi RA, Joshi RR. Org. Process Res. Dev. 2008; 12: 995
    • 48b Gage JR, Guo X, Tao J, Zheng C. Org. Process Res. Dev. 2012; 16: 930
  • 49 Van Alsten JG, Reeder LM, Stanchina CL, Knoechel DJ. Org. Process Res. Dev. 2008; 12: 989
    • 50a Buonomenna MG, Drioli E. Org. Process Res. Dev. 2008; 12: 982
    • 50b Park JH, Park CY, Song HS, Huh YS, Kim GH, Park CP. Org. Lett. 2013; 15: 752
    • 51a LaPorte TL, Hamedi M, DePue JS, Shen L, Watson D, Hsieh D. Org. Process Res. Dev. 2008; 12: 956
    • 51b Lévesque F, Seeberger PH. Org. Lett. 2011; 13: 5008
  • 52 Rossi E, Woehl P, Maggini M. Org. Process Res. Dev. 2012; 16: 1146
  • 53 Junior II, Flores MC, Sutili FK, Leite SG. F, Miranda LS. d. M, Leal IC. R, de Souza RO. M. A. Org. Process Res. Dev. 2012; 16: 1098
  • 54 Grongsaard P, Bulger PG, Wallace DJ, Tan L, Chen Q, Dolman SJ, Nyrop J, Hoerrner RS, Weisel M, Arredondo J, Itoh T, Xie C, Wen X, Zhao D, Muzzio DJ, Bassan EM, Schultz CS. Org. Process Res. Dev. 2012; 16: 1069
  • 55 van den Broek SA. M. W, Leliveld JR, Becker R, Delville MM. E, Nieuwland PJ, Koch K, Rutjes FP. J. T. Org. Process Res. Dev. 2012; 16: 934
  • 56 Loh G, Tanigawara R, Shaik SM, Sa-ei K, Wong L, Sharratt PN. Org. Process Res. Dev. 2012; 16: 958
    • 57a Oelgemöller M. Chem. Eng. Technol. 2012; 35: 1144
    • 57b Anderson BG, Bauta WE, Cantrell WR. Jr. Org. Process Res. Dev. 2012; 16: 967
  • 58 Abele S, Höck S, Schmidt G, Funel J.-A, Marti R. Org. Process Res. Dev. 2012; 16: 1114
  • 59 Johnson MD, May SA, Calvin JR, Remacle J, Stout JR, Diseroad WD, Zaborenko N, Haeberle BD, Sun W.-M, Miller MT, Brennan J. Org. Process Res. Dev. 2012; 16: 1017
  • 60 Wong LL, Wong RL, Loh G, Tan PE. W, Teoh SK, Shaik SM, Sharratt PN, Chew W, Tan ST, Wang D. Org. Process Res. Dev. 2012; 16: 1003
  • 61 Hartman RL. Org. Process Res. Dev. 2012; 16: 870
  • 62 Browne DL, Deadman BJ, Ashe R, Baxendale IR, Ley SV. Org. Process Res. Dev. 2011; 15: 693
  • 63 Gasparini G, Archer I, Jones E, Ashe R. Org. Process Res. Dev. 2012; 16: 1013
  • 64 Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
    • 65a Fu GC. Acc. Chem. Res. 2008; 41: 1555
    • 65b Lee BK, Biscoe MR, Buchwald SL. Tetrahedron Lett. 2009; 50: 3672
    • 65c González-Bobes F, Fu GC. J. Am. Chem. Soc. 2006; 128: 5360
    • 65d Buchwald SL, Mauger C, Mignani G, Scholz U. Adv. Synth. Catal. 2006; 348: 23
    • 65e Anderson KW, Buchwald SL. Angew. Chem. Int. Ed. 2005; 44: 6173
    • 65f Gelman D, Buchwald SL. Angew. Chem. Int. Ed. 2003; 42: 5993
  • 66 Fischmeister C, Doucet H. Green Chem. 2011; 13: 741
  • 67 Campbell AN, Stahl SS. Acc. Chem. Res. 2012; 45: 851
    • 68a Noël T, Buchwald SL. Chem. Soc. Rev. 2011; 40: 5010
    • 68b Naber JR, Buchwald SL. Angew. Chem. Int. Ed. 2010; 49: 9469
    • 69a Boorman TC, Larrosa I. Chem. Soc. Rev. 2011; 40: 1910
    • 69b Lu H, Zhang XP. Chem. Soc. Rev. 2011; 40: 1899
    • 69c Zhou M, Crabtree RH. Chem. Soc. Rev. 2011; 40: 1875
    • 69d Borovik AS. Chem. Soc. Rev. 2011; 40: 1870
    • 69e Gutekunst WR, Baran PS. Chem. Soc. Rev. 2011; 40: 1976
    • 69f Herrmann P, Bach T. Chem. Soc. Rev. 2011; 40: 2022
    • 69g Li B.-J, Yang S.-D, Shi Z.-J. Synlett 2008; 949
    • 69h Roduner E, Kaim W, Sarkar B, Urlacher VB, Pleiss J, Gläser R, Einicke W.-D, Sprenger GA, Beifuß U, Klemm E, Liebner C, Hieronymus H, Hsu S.-F, Pleitker B, Laschat S. ChemCatChem 2013; 5: 82
  • 70 McMurray L, O’Hara F, Gaunt MJ. Chem. Soc. Rev. 2011; 40: 1885
  • 71 Chen MS, White MC. Science (Washington, D.C.) 2010; 327: 566
  • 72 Lewis JC, Coelho PS, Arnold FH. Chem. Soc. Rev. 2011; 40: 2003
  • 73 Arata K. Green Chem. 2009; 11: 1719
  • 74 Bandini M, Tragni M. Org. Biomol. Chem. 2009; 7: 1501
  • 75 Swamy KC. K, Kumar NN. B, Balaraman E, Kumar KV. P. P. Chem. Rev. 2009; 109: 2551
  • 76 Hagiya K, Muramoto N, Misaki T, Sugimura T. Tetrahedron 2009; 65: 6109
  • 77 Emer E, Sinisi R, Capdevila MG, Petruzziello D, De Vincentiis F, Cozzi PG. Eur. J. Org. Chem. 2011; 647
  • 78 Bandini M, Cera G, Chiarucci M. Synthesis 2012; 44: 504
  • 79 Pattabiraman VR, Bode JW. Nature (London) 2011; 480: 471
  • 80 van Pelt S, Teeuwen RL. M, Janssen MH. A, Sheldon RA, Dunn PJ, Howard RM, Kumar R, Martínez I, Wong JW. Green Chem. 2011; 13: 1791
  • 81 Nuijens T, Cusan C, Kruijtzer JA. W, Rijkers DT. S, Liskamp RM. J, Quaedflieg PJ. L. M. J. Org. Chem. 2009; 74: 5145
    • 82a Komura K, Nakano Y, Koketsu M. Green Chem. 2011; 13: 828
    • 82b Lundberg H, Tinnis F, Adolfsson H. Chem. Eur. J. 2012; 18: 3822
    • 82c Allen CL, Chhatwal AR, Williams JM. J. Chem. Commun. 2012; 48: 666
    • 82d Charville H, Jackson DA, Hodges G, Whiting A, Wilson MR. Eur. J. Org. Chem. 2011; 5981
    • 82e Garcia-Álvarez R, Crochet P, Cadierno V. Green Chem. 2013; 15: 46
    • 82f Lanigan RM, Starkov P, Sheppard TD. J. Org. Chem. 2013; 78: 4512
  • 83 Kang B, Fu Z, Hong SH. J. Am. Chem. Soc. 2013; 135: 11704
  • 84 Grosjean C, Parker J, Thirsk C, Wright AR. Org. Process Res. Dev. 2012; 16: 781
  • 85 Liu X, Jensen KF. Green Chem. 2012; 14: 1471
  • 86 Subirós-Funosas R, Nieto-Rodriguez L, Jensen KJ, Albericio F. J. Pept. Sci. 2013; 19: 408
    • 87a Blackmond DG, Armstrong A, Coombe V, Wells A. Angew. Chem. Int. Ed. 2007; 46: 3798
    • 87b Simon M.-O, Li C.-J. Chem. Soc. Rev. 2012; 41: 1415
    • 87c Gawande MB, Bonifácio VD. B, Luque R, Branco PS, Varma RS. Chem. Soc. Rev. 2013; 42: 5522
  • 88 Narayan S, Muldoon J, Finn MG, Fokin VV, Kolb HC, Sharpless KB. Angew. Chem. Int. Ed. 2005; 44: 3275
  • 89 Chanda A, Fokin VV. Chem. Rev. 2009; 109: 725
  • 90 Tomasek J, Schatz J. Green Chem. 2013; 15: 2317
  • 91 Raj M, Singh VK. Chem. Commun. 2009; 6687
  • 92 Lipshutz BH, Ghoral S. Org. Lett. 2012; 14: 422
  • 93 Kus NS. Tetrahedron 2012; 68: 949
  • 94 Ager DJ, de Vries AH. M, de Vries JG. Chem. Soc. Rev. 2012; 41: 3340
  • 95 Duque R, Pogorzelec PJ, Cole-Hamilton DJ. Angew. Chem. Int. Ed. 2013; 52: 9805
    • 96a Morris RH. Chem. Soc. Rev. 2009; 38: 2282
    • 96b Wang C, Wu X, Xiao J. Chem. Asian J. 2008; 3: 1750
    • 96c Alonso F, Riente P, Yus M. Acc. Chem. Res. 2011; 44: 379
    • 97a Guillena G, Ramón DJ, Yus M. Chem. Rev. 2010; 110: 1611
    • 97b Dobereiner GE, Crabtree RH. Chem. Rev. 2010; 110: 681
  • 98 Haniti M, Hamid SA, Slatford PA, Williams JM. J. Adv. Synth. Catal. 2007; 349: 1555
  • 99 Magro AA. N, Eastham GR, Cole-Hamilton DJ. Chem. Commun. 2007; 3154
    • 100a Igarashi M, Fuchikami T. Tetrahedron Lett. 2001; 42: 1945
    • 100b Matsubara K, Iura T, Maki T, Nagashima H. J. Org. Chem. 2002; 67: 4985
    • 100c Motoyama Y, Mitsui K, Ishida T, Nagashima H. J. Am. Chem. Soc. 2005; 127: 13150
    • 100d Sasakuma H, Motoyama Y, Nagashima H. Chem. Commun. 2007; 4916
    • 100e Hanada S, Ishida T, Motoyama Y, Nagashima H. J. Org. Chem. 2007; 72: 7551
    • 100f Pelletier G, Bechara WS, Charette A. J. Am. Chem. Soc. 2010; 132: 12817
    • 101a Zhou S, Junge K, Addis D, Das S, Beller M. Angew. Chem. Int. Ed. 2009; 48: 9507
    • 101b Das S, Wendt B, Möller K, Junge K, Beller M. Angew. Chem. Int. Ed. 2012; 51: 1662