PDF herunterladen
de Vries, J. G.: 2018 Science of Synthesis, 2017/6: Catalytic Reduction in Organic Synthesis 2 DOI: 10.1055/sos-SD-227-00112
Catalytic Reduction in Organic Synthesis 2

2.5.2 Heterogeneous Catalytic Hydrogenation of Carboxylic Acids, Anhydrides, Esters, Amino Acids, and Amides

Weitere Informationen

Buch

Herausgeber: de Vries, J. G.

Autoren: Ayad, T. ; Bagal, D.; Besson, M.; Bhanage, B. ; Ciszek, B.; Claver, C.; Cole-Hamilton, D.; Fleischer, I. ; Hinze, S.; Ikariya, T.; Junge, K.; Kalck, P.; Kamer, P.; Kayaki, Y. ; Llopis, Q.; Matsunami, A.; Monguchi, Y.; Peñafiel, I.; Phansavath, P.; Pinel, C.; Puylaert, P.; Ratovelomanana-Vidal, V. ; Sajiki, H.; Savini, A.; Shi, Y.; Steinfeldt, N.; Urrutigoity, M.

Titel: Catalytic Reduction in Organic Synthesis 2

Print ISBN: 9783132406261; Online ISBN: 9783132406308; Buch-DOI: 10.1055/b-005-145235

1st edition © 2018. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

Science of Synthesis Reference Libraries



Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Reihenherausgeber: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Koch, G.; Molander, G. A.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Typ: Mehrbändiges Werk

Auch verfügbar auf
 


Abstract

The reduction of carboxylic acids and their derivatives (i.e., anhydrides, esters, amino acids, and amides) is a highly relevant transformation in synthetic organic chemistry and for biomass conversion. Interest in this area has recently increased thanks to the large-scale production of bio-based platform molecules. This chapter describes methods for the hydrogenation of carboxylic acids and derivatives using heterogeneous catalysts. The methods selected have generally been reported within the last ten years, and the focus is on those approaches that give high selectivity toward the desired products and on those employing highly stable catalysts.

Schlüsselwörter

hydrogenation - reduction - heterogeneous catalysis - carboxylic acids - carboxylic esters - alcohols - aldehydes - diols - amino alcohols - amines - carboxylic anhydrides - biomass-derived functionalized (di)acids - amino acids - amides - vapor-phase reduction - liquid-phase reduction
 
  • 1 Gribble GW. Chem. Soc. Rev. 1998; 27: 395
  • 2 Seyden-Penne J. Reductions by the Alumino- and Borohydrides in Organic Synthesis, 2nd ed.. Wiley; New York 1997
    Google Scholar
  • 3 McAlees AJ, McCrindle R. J. Chem. Soc. C 1969; 2425
  • 4 Clarke ML. Catal. Sci. Technol. 2012; 2: 2418
  • 5 Dub PA, Ikariya T. ACS Catal. 2012; 2: 1718
  • 6 Werkmeister S, Junge K, Beller M. Org. Process Res. Dev. 2014; 18: 289
  • 7 Gunanathan C, Milstein D. Chem. Rev. 2014; 114: 12024
  • 8 Korstanje TJ, van der Vlugt JI, Elsevier CJ, de Bruin B. Science (Washington, D. C.) 2015; 350: 298
  • 9 Pritchard J, Filonenko GA, van Putten R, Hensen EJM, Pidko EA. Chem. Soc. Rev. 2015; 44: 3808
  • 10 Yokoyama T, Yamagata N. Appl. Catal., A 2001; 221: 227
  • 11 Yokoyama T, Fujita N. Appl. Catal., A 2004; 276: 179
  • 12 Ferrero R.-M, Jacquot R. EP 539 274, 1992 Chem. Abstr.. 1993, 119, 138494
    Google Scholar
  • 13 Herrmann U, Emig G. Ind. Eng. Chem. Res. 1998; 37: 759
  • 14 Yu Y, Zhan W, Guo Y, Lu G, Adjimi S, Guo Y. J. Mol. Catal. A: Chem. 2014; 395: 392
  • 15 Yu Y, Guo Y, Zhan W, Guo Y, Wang Y, Lu G. J. Mol. Catal. A: Chem. 2014; 392: 1
  • 16 Bertone ME, Meyer CI, Regenhardt SA, Sebastian V, Garetto TF, Marchi AJ. Appl. Catal., A 2015; 503: 135
  • 17 Bertone ME, Regenhardt SA, Meyer CI, Sebastian V, Garetto TF, Marchi AJ. Top. Catal. 2016; 59: 159
  • 18 Zhang R, Yin H, Zhang D, Qi L, Lu H, Shen Y, Jiang T. Chem. Eng. J. (Amsterdam, Neth.) 2008; 140: 488
  • 19 Zhang D, Yin H, Xue J, Ge C, Jiang T, Yu L, Shen Y. Ind. Eng. Chem. Res. 2009; 48: 11220
  • 20 Liao X, Zhang Y, Hill M, Xia X, Zhao Y, Jiang Z. Appl. Catal., A 2014; 488: 256
  • 21 Budroni G, Corma A. J. Catal. 2008; 257: 403
  • 22 Jung SM, Godard E, Jung SY, Park K.-C, Choi JU. Catal. Today 2003; 87: 171
  • 23 Adkins H, Folkers K. J. Am. Chem. Soc. 1931; 53: 1095
  • 24 Turek T, Trimm DL, Cant NW. Catal. Rev. 1994; 36: 645
  • 25 Hattori H, Yamamoto K, Kaita J, Matsuda M, Yamada S. J. Am. Oil Chem. Soc. 2000; 77: 1283
  • 26 El Mansour A, Candy JP, Bournonville JP, Ferretti OA, Basset J.-M. Angew. Chem. Int. Ed. Engl. 1989; 28: 347
  • 27 Okumura K, Asakura K, Iwasawa Y. J. Phys. Chem. B 1997; 101: 9984
  • 28 Zhang B, Lin L, Zhuang J, Liu Y, Peng L, Jiang L. Molecules 2010; 15: 5139
  • 29 Zhu Y.-M, Shi XWL. Bull. Korean Chem. Soc. 2014; 35: 141
  • 30 Di W, Cheng J, Tian S, Li J, Chen J, Sun Q. Appl. Catal., A 2016; 510: 244
  • 31 Lu Z, Yin H, Wang A, Hu J, Xue W, Yin H, Liu S. J. Ind. Eng. Chem. 2016; 37: 208
  • 32 Yuan P, Liu Z, Zhang W, Sun H, Liu S. Chin. J. Catal. 2010; 31: 769
  • 33 Lin Q, Zheng H, Zheng G, Li X, Lou B. Int. J. Org. Chem. 2014; 4: 219
  • 34 Huang C, Zhang H, Zhao Y, Chen S, Liu Z. J. Colloid Interface Sci. 2012; 386: 60
  • 35 Narasimhan CS, Deshpande VM, Ramnarayan K. Appl. Catal., A 1989; 48: L1
  • 36 Pouilloux Y, Autin F, Guimon C, Barrault J. J. Catal. 1998; 176: 215
  • 37 Echeverri DA, Marin JM, Restrepo GM, Rios LA. Appl. Catal., A 2009; 366: 342
  • 38 Chen L.-F, Guo P.-J, Qiao M.-H, Yan S.-R, Li H.-X, Shen W, Xu H.-L. J. Catal. 2008; 257: 172
  • 39 Yin A, Wen C, Guo X, Dai W.-L, Fan K. J. Catal. 2011; 280: 77
  • 40 Kong X, Zhang X, Chen J. Catal. Commun. 2015; 65: 46
  • 41 Wang B, Wen C, Cui Y, Chen X, Dong Y, Dai W.-L. RSC Adv. 2015; 5: 29040
  • 42 Zheng J, Lin H, Wang Y.-n, Zheng X, Duan X, Yuan Y. J. Catal. 2013; 297: 110
  • 43 Silva AM, Morales MA, Baggio-Saitovitch EM, Jordão E, Fraga MA. Appl. Catal., A 2009; 353: 101
  • 44 Jiang H.-B, Jiang H.-J, Su K, Zhu D.-M, Zheng X.-L, Fu H.-Y, Chen H, Li R.-X. Appl. Catal., A 2012; 447: – 448: 164
  • 45 Liu S, Bischoff KM, Leathers TD, Qureshi N, Rich JO, Hughes SR. Bioresour. Technol. 2013; 143: 322
  • 46 Lee J.-M, Upare PP, Chang J.-S, Hwang YK, Lee JH, Kim YD, Kwon Y.-U. ChemSusChem 2014; 7: 2998
  • 47 Chen Y, Miller DJ, Jackson JE. Ind. Eng. Chem. Res. 2007; 46: 3334
  • 48 Li W, Ye L, Chen J, Duan X, Lin H, Yuan Y. Catal. Today 2015; 251: 53
  • 49 Xu G, Zhang J, Wang S, Zhao Y, Ma X. RSC Adv. 2016; 6: 51005
  • 50 Ito Y, Kawamato H, Saka S. Fuel 2016; 178: 118
  • 51 Broadbent HS, Campbell GC, Bartley WJ, Johnson JH. J. Org. Chem. 1959; 24: 1847
  • 52 Rieke RD, Thakur DS, Roberts BD, White GT. J. Am. Oil Chem. Soc. 1997; 74: 341
  • 53 Manyar HG, Paun C, Pilus R, Rooney DW, Thompson JM, Hardacre C. Chem. Commun. (Cambridge) 2010; 46: 6279
  • 54 Rozmysłowicz B, Kirilin A, Aho A, Manyar H, Hardacre C, Wärnå J, Salmi T, Murzin DYu. J. Catal. 2015; 328: 197
  • 55 Takeda Y, Nakagawa Y, Tomishige K. Catal. Sci. Technol. 2012; 2: 2221
  • 56 Kandel K, Chaudhary U, Nelson NC, Slowing II. ACS Catal. 2015; 5: 6719
  • 57 Cortright RD, Sanchez-Castillo M, Dumesic JA. Appl. Catal., B 2002; 39: 353
  • 58 Zhang Z, Jackson JE, Miller DJ. Appl. Catal., A 2001; 219: 89
  • 59 Primo A, Concepción P, Corma A. Chem. Commun. (Cambridge) 2011; 47: 3613
  • 60 Takeda Y, Shoji T, Watanabe H, Tamura M, Nakagawa Y, Okumura K, Tomishige K. ChemSusChem 2015; 8: 1170
  • 61 Akiyama S, Kakio T, Oikawa R, Ugou K, Hiraki R, Sano M, Suzuki T, Mitake T. J. Jpn. Pet. Inst. 2014; 57: 216
  • 62 Fabre L, Gallezot P, Perrard A. J. Catal. 2002; 208: 247
  • 63 Binder JB, Raines RT. J. Am. Chem. Soc. 2009; 131: 1979
  • 64 Delhomme C, Weuster-Botz D, Kühn FE. Green Chem. 2009; 11: 13
  • 65 Hong UG, Hwang S, Seo JG, Yi J, Song IK. Catal. Lett. 2010; 138: 28
  • 66 Hong UG, Park HW, Lee J, Hwang S, Song IK. J. Ind. Eng. Chem. 2012; 18: 462
  • 67 You C, Zhang C, Chen L, Qi Z. Appl. Organomet. Chem. 2015; 29: 653
  • 68 Zhang C, Chen L, Cheng H, Zhu X, Qi Z. Catal. Today 2016; 276: 55
  • 69 Tapin B, Epron F, Especel C, Ly BK, Pinel C, Besson M. ACS Catal. 2013; 3: 2327
  • 70 Minh DP, Besson M, Pinel C, Fuertes P, Petitjean C. Top. Catal. 2010; 53: 1270
  • 71 Ly BK, Minh DP, Pinel C, Besson M, Tapin B, Epron F, Especel C. Top. Catal. 2012; 55: 466
  • 72 Kang KH, Hong UG, Bang Y, Choi JH, Kim JK, Lee JK, Han SJ, Song IK. Appl. Catal., A 2015; 490: 153
  • 73 Liu X, Wang X, Xu G, Liu Q, Mu X, Liu H. J. Mater. Chem. A 2015; 3: 23560
  • 74 Takeda Y, Tamura M, Nakagawa Y, Okumura K, Tomishige K. Catal. Sci. Technol. 2016; 6: 5668
  • 75 Hong UG, Park HW, Lee J, Hwang S, Yi J, Song IK. Appl. Catal., A 2012; 415–416: 141
  • 76 Hong UG, Kim JK, Lee J, Lee JK, Song JH, Yi J, Song IK. J. Ind. Eng. Chem. 2014; 20: 3834
  • 77 Di X, Shao Z, Li C, Li W, Liang C. Catal. Sci. Technol. 2015; 5: 2441
  • 78 Li S, Wang X, Liu X, Xu G, Han S, Mu X. Catal. Commun. 2015; 61: 92
  • 79 Yu L, Du X.-L, Yuan J, Liu Y.-M, Cao Y, He H.-Y, Fan K.-N. ChemSusChem 2013; 6: 42
  • 80 Bozell JJ, Petersen GR. Green Chem. 2010; 12: 539
  • 81 Wright WRH, Palkovits R. ChemSusChem 2012; 5: 1657
  • 82 Alonso DM, Wettstein SG, Dumesic JA. Green Chem. 2013; 15: 584
  • 83 Manzer LE. WO 02 074 760, 2002 Chem. Abstr.. 2002, 137, 247597
    Google Scholar
  • 84 Al-Shaal MG, Wright WRH, Palkovits R. Green Chem. 2012; 14: 1260
  • 85 Raspolli Galletti AM, Antonetti C, De Luise V, Martinelli M. Green Chem. 2012; 14: 688
  • 86 Bourne RA, Stevens JG, Ke J, Poliakoff M. Chem. Commun. (Cambridge) 2007; 4632
  • 87 Hengne AM, Rode CV. Green Chem. 2012; 14: 1064
  • 88 van de Moesdijk CGM, Janssen PHJ. US 4 420 622, 1983 Chem. Abstr.. 1983, 98, 179201
    Google Scholar
  • 89 Yan ZP, Lin L, Liu S. Energy Fuels 2009; 23: 3853
  • 90 Folkers K, Adkins H. J. Am. Chem. Soc. 1932; 54: 1045
  • 91 Christian RV, Brown HD, Hixon R. J. Am. Chem. Soc. 1947; 69: 1961
  • 92 Du X.-L, Bi Q.-Y, Liu Y.-M, Cao Y, He H.-Y, Fan K.-N. Green Chem. 2012; 14: 935
  • 93 Li M, Li G, Li N, Wang A, Dong W, Wang X, Cong Y. Chem. Commun. (Cambridge) 2014; 50: 1414
  • 94 Corbel-Demailly L, Ly BK, Minh DP, Tapin B, Especel C, Epron F, Cabiac A, Guillon E, Besson M, Pinel C. ChemSusChem 2013; 6: 2388
  • 95 Meinzer A, Breckel A, Thaher BA, Manicone N, Otto HH. Helv. Chim. Acta 2004; 87: 90
  • 96 Tamura M, Tamura R, Takeda Y, Nakagawa Y, Tomishige K. Chem.–Eur. J. 2015; 21: 3097
  • 97 Pimparkar KP, Miller DJ, Jackson JE. Ind. Eng. Chem. Res. 2008; 47: 7648
  • 98 Jere FT, Miller DJ, Jackson JE. Org. Lett. 2003; 5: 527
  • 99 Tamura M, Tamura R, Takeda Y, Nakagawa Y, Tomishige K. Chem. Commun. (Cambridge) 2014; 50: 6656
  • 100 Metkar PS, Scialdone MA, Moloy KG. Green Chem. 2014; 16: 4575
  • 101 Smith AM, Whyman R. Chem. Rev. 2014; 114: 5477
  • 102 Wojcik B, Adkins H. J. Am. Chem. Soc. 1934; 56: 2419
  • 103 Adkins H. US 2 143 751, 1939 Chem. Abstr.. 1939, 33, 2906
    Google Scholar
  • 104 Broadbent HS, Bartley WJ. J. Org. Chem. 1963; 28: 2345
  • 105 Guyer A, Bieler A, Gerliczy G. Helv. Chim. Acta 1955; 38: 1649
  • 106 King RM. US 4 448 998, 1984 Chem. Abstr.. 1984, 101, 54551
    Google Scholar
  • 107 Hirosawa C, Wakasa N, Fuchikami T. Tetrahedron Lett. 1996; 37: 6749
  • 108 Beamson G, Papworth AJ, Philipps C, Smith AM, Whyman R. J. Catal. 2010; 269: 93
  • 109 Beamson G, Papworth AJ, Philipps C, Smith AM, Whyman R. Adv. Synth. Catal. 2010; 352: 869
  • 110 Beamson G, Papworth AJ, Philipps C, Smith AM, Whyman R. J. Catal. 2011; 278: 228
  • 111 Burch R, Paun C, Cao X.-M, Crawford P, Goodrich P, Hardacre C, Hu P, McLaughlin L, Sà J, Thompson JM. J. Catal. 2011; 283: 89
  • 112 Coetzee J, Manyar HG, Hardacre C, Cole-Hamilton DJ. ChemCatChem 2013; 5: 2843
  • 113 Stein M, Breit B. Angew. Chem. Int. Ed. 2013; 52: 2231