Download PDF
de Vries, J. G.: 2018 Science of Synthesis, 2017/6: Catalytic Reduction in Organic Synthesis 2 DOI: 10.1055/sos-SD-227-00014
Catalytic Reduction in Organic Synthesis 2

2.2 Transfer Hydrogenation of Ketones to Alcohols

More Information

Book

Editor: de Vries, J. G.

Authors: Ayad, T.; Bagal, D. B.; Besson, M.; Bhanage, B. M.; Ciszek, B.; Claver, C.; Cole-Hamilton, D. J.; Fleischer, I.; Hinze, S.; Ikariya, T.; Junge, K.; Kalck, P.; Kamer, P. C. J.; 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.; Urrutigoïty, M.

Title: Catalytic Reduction in Organic Synthesis 2

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

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

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

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

Type: Multivolume Edition

Also available at
 


Abstract

Transfer hydrogenation offers an alternative to hydrogenation using gaseous hydrogen, as well as a practical synthetic approach to enantiopure compounds. Alcohols, formic acid, and formate salts are often used as safe and nontoxic hydrogen sources in transition-metal catalyzed transfer hydrogenation systems. This chapter highlights effective transfer hydrogenation and asymmetric transfer hydrogenation of ketones catalyzed by transition-metal complexes. The reactions described in this section are classified according to the reducing agents employed and the type of ketone substrate.

Key words

transfer hydrogenation - asymmetric transfer hydrogenation - ketones - esters - alcohols - propan-2-ol - formic acid - formate salts - metal-ligand cooperation - dynamic kinetic resolution - reduction
 
  • 1 Chen Q.-A, Ye Z.-S, Duan Y, Zhou Y.-G. Chem. Soc. Rev. 2013; 42: 497
  • 2 Chelucci G, Baldino S, Baratta W. Acc. Chem. Res. 2015; 48: 363
  • 3 Fleury-Brégeot N, de la Fuente V, Castillón S, Claver C. ChemCatChem 2010; 2: 1346
  • 4 Kuwano R. Heterocycles 2008; 76: 909
  • 5 Hu X.-P, Wang D.-S, Yu C.-B, Zhou Y.-G, Zheng Z. Top. Organomet. Chem. 2011; 36: 313
  • 6 Wang D.-S, Chen Q.-A, Lu S.-M, Zhou Y.-G. Chem. Rev. 2012; 112: 2557
  • 7 Zhao D, Glorius F. Angew. Chem. Int. Ed. 2013; 52: 9616
  • 8 He Y.-M, Song F.-T, Fan Q.-H. Top. Curr. Chem. 2014; 343: 145
  • 9 Nagano T, Iimuro A, Yamaji K, Kita Y, Mashima K. Heterocycles 2014; 88: 103
  • 10 Zhang Z, Butt NA, Zhang W. Chem. Rev. 2016; 116: 14769
  • 11 Václavík J, Kačer P, Kuzma M, Červený L. Molecules 2011; 16: 5460
  • 12 Saidi O, Williams JMJ. Top. Organomet. Chem. 2011; 34: 77
  • 13 Sues PE, Demmans KZ, Morris RH. Dalton Trans. 2014; 43: 7650
  • 14 Wang D, Astruc D. Chem. Rev. 2015; 115: 6621
  • 15 Nedden HG, Zanotti-Gerosa A, Wills M. Chem. Rec. 2016; 16: 2623
  • 16 Ikariya T, Blacker AJ. Acc. Chem. Res. 2007; 40: 1300
  • 17 Wang C, Wu X, Xiao J. Chem.–Asian J. 2008; 3: 1750
  • 18 Foubelo F, Nájera C, Yus M. Tetrahedron: Asymmetry 2015; 26: 769
  • 19 Foubelo F, Yus M. Chem. Rec. 2015; 15: 907
  • 20 Wills M. Top. Curr. Chem. 2016; 374: 14
  • 21 Wu X, Xiao J. Chem. Commun. (Cambridge) 2007; 2449
  • 22 He Y.-M, Fan Q.-H. ChemCatChem 2015; 7: 398
  • 23 Wei Y, Wu X, Wang C, Xiao J. Catal. Today 2015; 247: 104
  • 24 Wu X, Wang C, Xiao J. Chem. Rec. 2016; 16: 2772
  • 25 Malacea R, Poli R, Manoury E. Coord. Chem. Rev. 2010; 254: 729
  • 26 Štephan B, Požgan F. Catal. Rev. Sci. Eng. 2014; 56: 82
  • 27 Wu X, Xiao J, In: Comprehensive Organic Synthesis Knochel P, Molander GA. Elsevier Amsterdam 2014; 8. 198
  • 28 Matsunami A, Kayaki Y. Tetrahedron Lett. 2018; 59: 504
  • 29 Zhao B, Han Z, Ding K. Angew. Chem. Int. Ed. 2013; 52: 4744
  • 30 Khusnutdinova JR, Milstein D. Angew. Chem. Int. Ed. 2015; 54: 12236
  • 31 Kuwata S, Ikariya T. Dalton Trans. 2010; 39: 2984
  • 32 Ikariya T. Bull. Chem. Soc. Jpn. 2011; 84: 1
  • 33 Eisenstein O, Crabtree RH. New J. Chem. 2013; 37: 21
  • 34 Zheng C, You S.-L. Chem. Soc. Rev. 2012; 41: 2498
  • 35 Zhu C, Saito K, Yamanaka M, Akiyama T. Acc. Chem. Res. 2015; 48: 388
  • 36 Cohen R, Graves CR, Nguyen S.-BT, Martin JML, Ratner MA. J. Am. Chem. Soc. 2004; 126: 14796
  • 37 Henbest HB, Mitchell TRB. J. Chem. Soc. C 1970; 785
  • 38 Sasson Y, Blum J. J. Org. Chem. 1975; 40: 1887
  • 39 Chowdhury RL, Bäckvall J.-E. J. Chem. Soc., Chem. Commun. 1991; 1063
  • 40 Shvo Y, Czarkie D, Rahamim Y, Chodosh DF. J. Am. Chem. Soc. 1986; 108: 7400
  • 41 Fleischer S, Zhou S, Junge K, Beller M. Angew. Chem. Int. Ed. 2013; 52: 5120
  • 42 Jin W, Wang L, Yu Z. Organometallics 2012; 31: 5664
  • 43 Zhao M, Yu Z, Yan S, Li Y. Tetrahedron Lett. 2009; 50: 4624
  • 44 Chai H, Liu T, Wang Q, Yu Z. Organometallics 2015; 34: 5278
  • 45 Liu T, Chai H, Wang L, Yu Z. Organometallics 2017; 36: 2914
  • 46 Du W, Wang L, Wu P, Yu Z. Chem.–Eur. J. 2012; 18: 11550
  • 47 Chai H, Wang Q, Liu T, Yu Z. Dalton Trans. 2016; 45: 17843
  • 48 Wang Q, Chai H, Yu Z. Organometallics 2017; 36: 3638
  • 49 Zhang Y, Li X, Hong SH. Adv. Synth. Catal. 2010; 352: 1779
  • 50 Ghoochany LT, Farsadpour S, Sun Y, Thiel WR. Eur. J. Inorg. Chem. 2011; 3431
  • 51 Shi J, Hu B, Gong D, Shang S, Hou G, Chen D. Dalton Trans. 2016; 45: 4828
  • 52 Baratta W, Ballico M, Del Zotto A, Herdweck E, Magnolia S, Peloso R, Siega K, Toniutti M, Zangrando E, Rigo P. Organometallics 2009; 28: 4421
  • 53 Baratta W, Ballico M, Esposito G, Rigo P. Chem.–Eur. J. 2008; 14: 5588
  • 54 Lundgren RJ, Rankin MA, McDonald R, Schatte G, Stradiotto M. Angew. Chem. Int. Ed. 2007; 46: 4732
  • 55 Witt J, Pöthig A, Kühn FE, Baratta W. Organometallics 2013; 32: 4042
  • 56 Liu PN, Ju KD, Lau CP. Adv. Synth. Catal. 2011; 353: 275
  • 57 Lundgren RJ, Stradiotto M. Chem.–Eur. J. 2008; 14: 10388
  • 58 Ruff A, Kirby C, Chan BC, OʼConnor AR. Organometallics 2016; 35: 327
  • 59 Wei Y, Xue D, Lei Q, Wang C, Xiao J. Green Chem. 2013; 15: 629
  • 60 Talwar D, Wu X, Saidi O, Poyatos Salguero N, Xiao J. Chem.–Eur. J. 2014; 20: 12835
  • 61 Hashiguchi S, Fujii A, Takehara J, Ikariya T, Noyori R. J. Am. Chem. Soc. 1995; 117: 7562
  • 62 Dub PA, Ikariya T. J. Am. Chem. Soc. 2013; 135: 2604
  • 63 Gao J.-X, Ikariya T, Noyori R. Organometallics 1996; 15: 1087
  • 64 Takehara J, Hashiguchi S, Fujii A, Inoue S, Ikariya T, Noyori R. Chem. Commun. (Cambridge) 1996; 233
  • 65 Zuo W, Lough AJ, Li YF, Morris RH. Science (Washington, D. C.) 2013; 342: 1080
  • 66 Pannetier N, Sortais J.-B, Issenhuth J.-T, Barloy L, Sirlin C, Holuigue A, Lefort L, Panella L, de Vries JG, Pfeffer M. Adv. Synth. Catal. 2011; 353: 2844
  • 67 Wakeham RJ, Morris JA, Williams JMJ. ChemCatChem 2015; 7: 4039
  • 68 Fujii A, Hashiguchi S, Uematsu N, Ikariya T, Noyori R. J. Am. Chem. Soc. 1996; 118: 2521
  • 69 Hayes AM, Morris DJ, Clarkson GJ, Wills M. J. Am. Chem. Soc. 2005; 127: 7318
  • 70 Soni R, Jolley KE, Clarkson GJ, Wills M. Org. Lett. 2013; 15: 5110
  • 71 Touge T, Hakamata T, Nara H, Kobayashi T, Sayo N, Saito T, Kayaki Y, Ikariya T. J. Am. Chem. Soc. 2011; 133: 14960
  • 72 Kišić A, Stephan M, Mohar B. Adv. Synth. Catal. 2015; 357: 2540
  • 73 Touge T, Nara H, Fujiwhara M, Kayaki Y, Ikariya T. J. Am. Chem. Soc. 2016; 138: 10084
  • 74 Wu X, Li X, King F, Xiao J. Angew. Chem. Int. Ed. 2005; 44: 3407
  • 75 Wu X, Li X, Zanotti-Gerosa A, Pettman A, Liu J, Mills AJ, Xiao J. Chem.–Eur. J. 2008; 14: 2209
  • 76 Wu X, Vinci D, Ikariya T, Xiao J. Chem. Commun. (Cambridge) 2005; 4447
  • 77 Matsumura K, Hashiguchi S, Ikariya T, Noyori R. J. Am. Chem. Soc. 1997; 119: 8738
  • 78 Shatskiy A, Kivijärvi T, Lundberg H, Tinnis F, Adolfsson H. ChemCatChem 2015; 7: 3818
  • 79 Fang Z, Wills M. J. Org. Chem. 2013; 78: 8594
  • 80 Fang Z, Wills M. Org. Lett. 2014; 16: 374
  • 81 Peach P, Cross DJ, Kenny JA, Mann I, Houson I, Campbell L, Walsgrove T, Wills M. Tetrahedron 2006; 62: 1864
  • 82 Li X, Li L, Tang Y, Zhong L, Cun L, Zhu J, Liao J, Deng J. J. Org. Chem. 2010; 75: 2981
  • 83 Tang L, Lin Z, Wang Q, Wang X, Cun L, Yuan W, Zhu J, Deng J. Tetrahedron Lett. 2012; 53: 3828
  • 84 Tsuchiya Y, Hamashima Y, Sodeoka M. Org. Lett. 2006; 8: 4851
  • 85 Alonso DA, Brandt P, Nordin SJM, Andersson PG. J. Am. Chem. Soc. 1999; 121: 9580
  • 86 Yamakawa M, Ito H, Noyori R. J. Am. Chem. Soc. 2000; 122: 1466
  • 87 Matsuoka A, Sandoval CA, Uchiyama M, Noyori R, Naka H. Chem.–Asian J. 2015; 10: 112
  • 88 Li J, Tang Y, Wang Q, Li X, Cun L, Zhang X, Zhu J, Li L, Deng J. J. Am. Chem. Soc. 2012; 134: 18522
  • 89 Reetz MT, Li X. J. Am. Chem. Soc. 2006; 128: 1044
  • 90 Hamada T, Torii T, Izawa K, Noyori R, Ikariya T. Org. Lett. 2002; 4: 4373
  • 91 Hamada T, Torii T, Izawa K, Ikariya T. Tetrahedron 2004; 60: 7411
  • 92 Wang F, Liu H, Cun L, Zhu J, Deng J, Jiang Y. J. Org. Chem. 2005; 70: 9424
  • 93 Ma Y, Liu H, Chen L, Cui X, Zhu J, Deng J. Org. Lett. 2003; 5: 2103
  • 94 Yuki Y, Touge T, Nara H, Matsumura K, Fujiwhara M, Kayaki Y, Ikariya T. Adv. Synth. Catal. 2018; 360: 568
  • 95 Fuglseth E, Sundby E, Hoff BH. J. Fluorine Chem. 2009; 130: 600
  • 96 Šterk D, Stephan M, Mohar B. Org. Lett. 2006; 8: 5935
  • 97 Perryman MS, Harris ME, Foster JL, Joshi A, Clarkson GJ, Fox DJ. Chem. Commun. (Cambridge) 2013; 49: 10022
  • 98 Soltani O, Ariger MA, Vázquez-Villa H, Carreira EM. Org. Lett. 2010; 12: 2893
  • 99 Vázquez-Villa H, Reber S, Ariger MA, Carreira EM. Angew. Chem. Int. Ed. 2011; 50: 8979
  • 100 Lee D.-M, Kwak SH, Lee K.-I. Bull. Korean Chem. Soc. 2009; 30: 1317
  • 101 Kosmalski T, Wojtczak A, Zaidlewicz M. Tetrahedron: Asymmetry 2009; 20: 1138
  • 102 Xu Z, Zhu S, Liu Y, He L, Geng Z, Zhang Y. Synthesis 2010; 811
  • 103 Geng Z, Wu Y, Miao S, Shen Z, Zhang Y. Tetrahedron Lett. 2011; 52: 907
  • 104 Zhang D, Cheng T, Zhao Q, Xu J, Liu G. Org. Lett. 2014; 16: 5764
  • 105 Leijondahl K, Fransson A.-BL, Bäckvall J.-E. J. Org. Chem. 2006; 71: 8622
  • 106 Cotman AE, Cahard D, Mohar B. Angew. Chem. Int. Ed. 2016; 55: 5294
  • 107 Ariger MA, Carreira EM. Org. Lett. 2012; 14: 4522
  • 108 Lin Z, Li J, Huang Q, Huang Q, Wang Q, Tang L, Gong D, Yang J, Zhu J, Deng J. J. Org. Chem. 2015; 80: 4419
  • 109 Zhao Q, Zhao Y, Liao H, Cheng T, Liu G. ChemCatChem 2016; 8: 412
  • 110 Pellissier H. Tetrahedron 2011; 67: 3769
  • 111 Echeverria P.-G, Ayad T, Phansavath P, Ratovelomanana-Vidal V. Synthesis 2016; 48: 2523
  • 112 Murata K, Okano K, Miyagi M, Iwane H, Noyori R, Ikariya T. Org. Lett. 1999; 1: 1119
  • 113 Verho O, Bäckvall J.-E. J. Am. Chem. Soc. 2015; 137: 3996
  • 114 Sato Y, Kayaki Y, Ikariya T. Chem. Commun. (Cambridge) 2012; 58: 3635
  • 115 Bai J, Miao S, Wu Y, Zhang Y. Chin. J. Chem. 2011; 29: 2476
  • 116 Liu Z, Shultz CS, Sherwood CA, Krska S, Dormer PG, Desmond R, Lee C, Sherer EC, Shpungin J, Cuff J, Xu F. Tetrahedron Lett. 2011; 52: 1685
  • 117 Echeverria P.-G, Cornil J, Férard C, Guérinot A, Cossy J, Phansavath P, Ratovelomanana-Vidal V. RSC Adv. 2015; 5: 56815
  • 118 Monnereau L, Cartigny D, Scalone M, Ayad T, Ratovelomanana-Vidal V. Chem.–Eur. J. 2015; 21: 11799
  • 119 Limanto J, Krska SW, Dorner BT, Vazquez E, Yoshikawa N, Tan L. Org. Lett. 2010; 12: 512
  • 120 Kumaraswamy G, Murthy AN, Narayanarao V, Vemulapalli SPB, Bharatam J. Org. Biomol. Chem. 2013; 11: 6751
  • 121 Wu Y, Geng Z, Bai J, Zhang Y. Chin. J. Chem. 2011; 29: 1467
  • 122 Son S.-M, Lee H.-K. J. Org. Chem. 2014; 79: 2666
  • 123 Ding Z, Yang J, Wang T, Shen Z, Zhang Y. Chem. Commun. (Cambridge) 2009; 571
  • 124 Wu G, Zhu J, Ding Z, Shen Z, Zhang Y. Tetrahedron Lett. 2009; 50: 427
  • 125 Steward KM, Corbett MT, Goodman CG, Johnson JS. J. Am. Chem. Soc. 2012; 134: 20197
  • 126 Steward KM, Corbett MT, Goodman CG, Johnson JS. J. Am. Chem. Soc. 2015; 137: 3991
  • 127 Goodman CG, Do DT, Johnson JS. Org. Lett. 2013; 15: 2446
  • 128 Corbett MT, Johnson JS. J. Am. Chem. Soc. 2013; 135: 594
  • 129 Steward KM, Gentry EC, Johnson JS. J. Am. Chem. Soc. 2012; 134: 7329
  • 130 Steward KM, Gentry EC, Johnson JS. J. Am. Chem. Soc. 2015; 137: 3715
  • 131 Fernández R, Ros A, Magriz A, Dietrich H, Lassaletta JM. Tetrahedron 2007; 63: 6755
  • 132 Ros A, Magriz A, Dietrich H, Lassaletta JM, Fernández R. Tetrahedron 2007; 63: 7532
  • 133 Vyas VK, Bhanage BM. Org. Lett. 2016; 18: 6436
  • 134 Cheng T, Ye Q, Zhao Q, Liu G. Org. Lett. 2015; 17: 4972
  • 135 Dub PA, Ikariya T. ACS Catal. 2012; 2: 1718
  • 136 Werkmeister S, Junge K, Beller M. Org. Process Res. Dev. 2014; 18: 289
  • 137 Lee S.-H, Nikonov GI. ChemCatChem 2015; 7: 107
  • 138 Dubey A, Khaskin E. ACS Catal. 2016; 6: 3998
  • 139 Spasyuk D, Smith S, Gusev DG. Angew. Chem. Int. Ed. 2013; 52: 2538