Skip to main content
Log in

Metal-Catalysed Transfer Hydrogenation of Ketones

  • Review
  • Published:
Topics in Current Chemistry Aims and scope Submit manuscript

Abstract

We highlight recent developments of catalytic transfer hydrogenation of ketones promoted by transition metals, while placing it within its historical context. Since optically active secondary alcohols are important building blocks in fine chemicals synthesis, the focus of this review is devoted to chiral catalyst types which are capable of inducing high stereoselectivities. Ruthenium complexes still represent the largest part of the catalysts, but other metals (e.g. Fe) are rapidly penetrating this field. While homogeneous transfer hydrogenation catalysts in some cases approach enzymatic performance, the interest in heterogeneous catalysts is constantly growing because of their reusability. Despite excellent activity, selectivity and compatibility of metal complexes with a variety of functional groups, no universal catalysts exist. Development of future catalyst systems is directed towards reaching as high as possible activity with low catalyst loadings, using “greener” conditions, and being able to operate under mild conditions and in a highly selective manner for a broad range of substrates.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14
Fig. 15
Fig. 16
Fig. 17
Fig. 18
Fig. 19
Fig. 20
Fig. 21
Fig. 22
Fig. 23
Fig. 24
Fig. 25
Fig. 26
Fig. 27
Fig. 28
Fig. 29
Fig. 30
Fig. 31
Fig. 32
Fig. 33
Fig. 34
Fig. 35
Fig. 36
Fig. 37
Fig. 38
Fig. 39
Fig. 40
Fig. 41
Fig. 42
Fig. 43
Fig. 44
Fig. 45
Fig. 46
Fig. 47
Fig. 48
Fig. 49
Fig. 50
Fig. 51
Fig. 52
Fig. 53
Fig. 54
Fig. 55
Fig. 56
Fig. 57
Fig. 58
Fig. 59
Fig. 60
Fig. 61
Fig. 62
Fig. 63
Fig. 64
Fig. 65
Fig. 66
Fig. 67
Fig. 68
Fig. 69
Fig. 70
Fig. 71
Fig. 72

We’re sorry, something doesn't seem to be working properly.

Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

References

  1. Blaser HU, Malan C, Pugin B, Spindler F, Steiner H, Studer M (2003) Adv Synth Catal 345:103

    Article  CAS  Google Scholar 

  2. Ohkuma T (2010) Proc Jpn Acad B 86:202

    Article  CAS  Google Scholar 

  3. Arai N, Ohkuma T (2011) In: Molander GA (ed) Science of synthesis: stereoselective synthesis, vol 2. Thieme, Stuttgart, pp 9–57

    Google Scholar 

  4. Noyori R, Ohkuma T (2001) Angew Chem Int Ed 40:40

    Article  CAS  Google Scholar 

  5. Klingler FD (2007) Acc Chem Res 40:1367

    Article  CAS  Google Scholar 

  6. Palmer MJ, Wills M (1999) Tetrahedron Asymmetry 10:2045

    Article  CAS  Google Scholar 

  7. Ikariya T, Blacker AJ (2007) Acc Chem Res 40:1300

    Article  CAS  Google Scholar 

  8. Václavik J, Kačer P, Kuzma M, Červený L (2011) Molecules 16:5460

    Article  CAS  Google Scholar 

  9. Gladiali S, Alberico E (2006) Chem Soc Rev 35:226

    Article  CAS  Google Scholar 

  10. Hashiguchi S, Fujii A, Haack KJ, Matsumura K, Ikariya T, Noyori R (1997) Angew Chem Int Ed 36:288

    Article  CAS  Google Scholar 

  11. Fujii A, Hashiguchi S, Uematsu N, Ikariya T, Noyori R (1996) J Am Chem Soc 118:2521

    Article  CAS  Google Scholar 

  12. Zweifel T, Naubron JV, Büttner T, Ott T, Grützmacher H (2008) Angew Chem Int Ed 47:3245

    Article  CAS  Google Scholar 

  13. Sharma AK, Joshi H, Sharma KN, Gupta PL, Singh AK (2014) Organometallics 33:3629

    Article  CAS  Google Scholar 

  14. Maytum HC, Tavassoli B, Williams JMJ (2007) Org Lett 9:4387

    Article  CAS  Google Scholar 

  15. Nixon TD, Whittlesey MK, Williams JMJ (2011) Tetrahedron Lett 52:6652

    Article  CAS  Google Scholar 

  16. Guyon C, Métay E, Duguet N, Lemaire M (2013) Eur J Org Chem 5439

  17. Schmidt R, Meerwein H (1925) Justus Liebigs Ann Chem 444:221

    Article  Google Scholar 

  18. Verley A (1925) Bull Soc Fr 37:537

    CAS  Google Scholar 

  19. Ponndorf W (1926) Angew Chem 39:138

    Article  CAS  Google Scholar 

  20. Doering WE, Young RW (1950) J Am Chem Soc 72:631

    Article  CAS  Google Scholar 

  21. Haddad YMY, Henbest HB, Husbands J, Mitchell TRB (1964) Proc Chem Soc Lond 361

  22. Henbest HB, Mitchell TRB (1970) J Chem Soc C 785

  23. Sasson Y, Blum J (1975) J Org Chem 40:1887

    Article  CAS  Google Scholar 

  24. Chowdhury RL, Bäckvall JE (1991) J Chem Soc Chem Commun 1063

  25. Shvo Y, Czarkie D, Rahamim Y, Chodosh DF (1986) J Am Chem Soc 108:7400

    Article  CAS  Google Scholar 

  26. Conley BL, Pennington-Boggio MK, Boz E, Williams TJ (2010) Chem Rev 110:2294

    Article  CAS  Google Scholar 

  27. Manzini S, Blanco CAU, Nolan SP (2012) Adv Synth Catal 354:3036

    Article  CAS  Google Scholar 

  28. Liu PN, Ju KD, Lau CP (2011) Adv Synth Catal 353:275

    Article  CAS  Google Scholar 

  29. Kumar M, DePasquale J, White NJ, Zeller M, Papish ET (2013) Organometallics 32:2135

    Article  CAS  Google Scholar 

  30. Ghoochany LT, Farsadpour S, Sun Y, Thiel WR (2011) Eur J Inorg Chem 3431

  31. Zhao M, Yu Z, Yan S, Li Y (2009) Tetrahedron Lett 50:4624–4628

    Article  CAS  Google Scholar 

  32. Zhao M, Yu Z, Yan S, Li Y (2009) J Organomet Chem 694:3068

    Article  CAS  Google Scholar 

  33. Jin W, Wang L, Yu Z (2012) Organometallics 31:5664

    Article  CAS  Google Scholar 

  34. Deng H, Yu Z, Dong J, Wu S (2005) Organometallics 24:4110

    Article  CAS  Google Scholar 

  35. Zhu Z, Zhang J, Fu H, Yuan M, Zheng X, Chen H, Li R (2014) RSC Adv 4:52734

    Article  CAS  Google Scholar 

  36. Du W, Wang L, Wu P, Yu Z (2012) Chem Eur J 18:11550

    Article  CAS  Google Scholar 

  37. Zhang Y, Li X, Hong SH (2010) Adv Synth Catal 352:1779

    Article  CAS  Google Scholar 

  38. Clapham SE, Hadzovic A, Morris RH (2004) Coord Chem Rev 248:2201

    Article  CAS  Google Scholar 

  39. Samec JSM, Bäckvall JE, Andersson PG, Brandt P (2006) Chem Soc Rev 35:237

    Article  CAS  Google Scholar 

  40. Hashiguchi S, Fujii A, Takehara J, Ikariya T, Noyori R (1995) J Am Chem Soc 117:7562

    Article  CAS  Google Scholar 

  41. Palmer M, Walsgrove T, Wills M (1997) J Org Chem 62:5226

    Article  CAS  Google Scholar 

  42. Alonso DA, Guijarro D, Pinho P, Temme O, Andersson PG (1998) J Org Chem 63:2749

    Article  CAS  Google Scholar 

  43. Yamakawa M, Yamada I, Noyori R (2001) Angew Chem Int Ed 40:2818

    Article  CAS  Google Scholar 

  44. Noyori R, Yamakawa M, Hashiguchi S (2001) J Org Chem 66:7931

    Article  CAS  Google Scholar 

  45. Yamakawa M, Ito H, Noyori R (2000) J Am Chem Soc 122:1466

    Article  CAS  Google Scholar 

  46. Alonso DA, Brandt P, Nordin SJM, Andersson PG (1999) J Am Chem Soc 121:9580

    Article  CAS  Google Scholar 

  47. Brandt P, Roth P, Andersson PG (2004) J Org Chem 69:4885

    Article  CAS  Google Scholar 

  48. Casey CP, Johnson JB (2003) J Org Chem 68:1998

    Article  CAS  Google Scholar 

  49. Pàmies O, Bäckvall JE (2001) Chem Eur J 7:5052

    Article  Google Scholar 

  50. Dub PA, Ikariya T (2013) J Am Chem Soc 135:2604

    Article  CAS  Google Scholar 

  51. Martins JED, Clarkson GJ, Wills M (2009) Org Lett 11:847

    Article  CAS  Google Scholar 

  52. Soni R, Cheung FK, Clarkson GC, Martins JED, Graham MA, Wills M (2011) Org Biomol Chem 9:3290

    Article  CAS  Google Scholar 

  53. Baratta W, Rigo P (2008) Eur J Inorg Chem 4041

  54. Everaere K, Mortreux A, Carpentier JF (2003) Adv Synth Catal 345:67

    Article  CAS  Google Scholar 

  55. Roszkowski P, Maurin JK, Czarnocki Z (2012) Tetrahedron Asymmetry 23:1106

    Article  CAS  Google Scholar 

  56. Roszkowski P, Maurin JK, Czarnocki Z (2013) Tetrahedron Asymmetry 24:643

    Article  CAS  Google Scholar 

  57. Soni R, Collinson JM, Clarkson GC, Wills M (2011) Org Lett 13:4304

    Article  CAS  Google Scholar 

  58. Cheung FK, Lin C, Minissi F, Crivillé AL, Graham MA, Fox DJ, Wills M (2007) Org Lett 9:4659

    Article  CAS  Google Scholar 

  59. Fang Z, Wills M (2013) J Org Chem 78:8594

    Article  CAS  Google Scholar 

  60. Touge T, Hakamata T, Nara H, Kobayashi T, Sayo N, Saito T, Kayaki Y, Ikariya T (2011) J Am Chem Soc 133:14960

    Article  CAS  Google Scholar 

  61. Cheung FK, Graham MA, Minissi F, Wills M (2007) Organometallics 26:5346

    Article  CAS  Google Scholar 

  62. Kišić A, Stephan M, Mohar B (2013) Org Lett 15:1614

    Article  CAS  Google Scholar 

  63. Kišić A, Stephan M, Mohar B (2014) Adv Synth Catal 356:3193

    Article  CAS  Google Scholar 

  64. Hayes AM, Morris DJ, Clarkson GJ, Wills M (2005) J Am Chem Soc 127:7318

    Article  CAS  Google Scholar 

  65. Facchetti G, Gandolfi R, Fusé M, Zerla D, Cesarotti E, Pellizzoni M, Rimoldi I (2015) New J Chem 39:3792

    Article  CAS  Google Scholar 

  66. Takehara J, Hashiguchi S, Fujii A, Inoue S, Ikariya T, Noyori R (1996) Chem Commun 233

  67. Deshpande SH, Kelkar AA, Gonnade RG, Shingote SK, Chaudhari RV (2010) Catal Lett 138:231

    Article  CAS  Google Scholar 

  68. Chakka SK, Andersson PG, Maguire GEM, Kruger HG, Govender T (2010) Eur J Org Chem 972

  69. Han ML, Hu XP, Huang JD, Chen LG, Zheng Z (2011) Tetrahedron Asymmetry 22:222

    Article  CAS  Google Scholar 

  70. Huynh KD, Ibrahim H, Kolodziej E, Toffano M, Vo-Thanh G (2011) New J Chem 35:2622

    Article  CAS  Google Scholar 

  71. Pastó M, Riera A, Pericàs MA (2002) Eur J Org Chem 2337

  72. Babin M, Clément R, Gagnon J, Fontaine FG (2012) New J Chem 36:1548

    Article  CAS  Google Scholar 

  73. Johnson TC, Totty WG, Wills M (2012) Org Lett 14:5230

    Article  CAS  Google Scholar 

  74. Darwish MO, Wallace A, Clarkson GJ, Wills M (2013) Tetrahedron Lett 54:4250

    Article  CAS  Google Scholar 

  75. Cambeiro XC, Pericàs MA (2011) Adv Synth Catal 353:113

    Article  CAS  Google Scholar 

  76. Sheeba MM, Tamizh M, Farruiga LJ, Endo A, Karvembu R (2014) Organometallics 33:540

    Article  CAS  Google Scholar 

  77. Ye W, Zhao M, Yu Z (2012) Chem Eur J 18:10843

    Article  CAS  Google Scholar 

  78. Ito J, Teshima T, Nishiyama H (2012) Chem Commun 48:1105

    Article  CAS  Google Scholar 

  79. Reetz MT, Li X (2006) J Am Chem Soc 128:1044

    Article  CAS  Google Scholar 

  80. Wettergren J, Buitrago E, Ryberg P, Adolfsson H (2009) Chem Eur J 15:5709

    Article  CAS  Google Scholar 

  81. Lundberg H, Adolfsson H (2011) Tetrahedron Lett 52:2754

    Article  CAS  Google Scholar 

  82. Coll M, Pàmies O, Adolfsson H, Diéguez M (2011) Chem Commun 47:12188

    Article  CAS  Google Scholar 

  83. Baratta W, Chelucci G, Herdtweck E, Magnolia S, Siega K, Rigo P (2007) Angew Chem Int Ed 46:7651

    Article  CAS  Google Scholar 

  84. Baratta W, Benedetti F, Del Zotto A, Fanfoni L, Felluga F, Magnolia S, Putignano E, Rigo P (2010) Organometallics 29:3563

    Article  CAS  Google Scholar 

  85. Zirakzadeh A, Schuecker R, Gorgas N, Mereiter K, Spindler F, Weissensteiner W (2012) Organometallics 31:4241

    Article  CAS  Google Scholar 

  86. Işık U, Aydemir M, Meriç N, Durap F, Kayan C, Temel H, Baysal A (2013) J Mol Catal A 379:225

    Article  CAS  Google Scholar 

  87. Spogliarich R, Zassinovich G, Kaspar J, Graziani M (1982) J Mol Catal 16:359

    Article  CAS  Google Scholar 

  88. Malacea R, Poli R, Manoury E (2010) Coord Chem Rev 254:729

    Article  CAS  Google Scholar 

  89. Tang L, Wang Q, Wang J, Lin Z, Wang X, Cun L, Yuan W, Zhu J, Lia J, Deng J (2012) Tetrahedron Lett 53:3839

    Article  CAS  Google Scholar 

  90. Fuentes JA, Carpenter I, Kann N, Clarke ML (2013) Chem Commun 49:10245

    Article  CAS  Google Scholar 

  91. Xu YQ, Yu SL, Li YY, Dong ZR, Gao JX (2013) Chin Chem Lett 24:527

    Article  CAS  Google Scholar 

  92. Liu WP, Yuan ML, Yang XH, Li K, Xie JH, Zhou QL (2015) Chem Commun 51:6123

    Article  CAS  Google Scholar 

  93. Pannetier N, Sortais JB, Issenhuth JT, Barloy L, Sirlin C, Holuigue A, Lefort L, Panella L, de Vries JG, Pfeffer M (2011) Adv Synth Catal 353:2844

    Article  CAS  Google Scholar 

  94. Coll M, Ahlford K, Pàmies O, Adolfsson H, Diéguez M (2012) Adv Synth Catal 354:415

    Article  CAS  Google Scholar 

  95. Coll M, Pàmies O, Diéguez M (2014) Adv Synth Catal 356:2293

    Article  CAS  Google Scholar 

  96. Coll M, Pàmies O, Adolfsson H, Diéguez M (2013) ChemCatChem 5:3821

    Article  CAS  Google Scholar 

  97. Tinnis F, Adolfsson H (2010) Org Biomol Chem 8:4536

    Article  CAS  Google Scholar 

  98. Aupoix A, Bournaud C, Vo-Thanh G (2011) Eur J Org Chem 2772

  99. Cross DJ, Houson I, Kawamoto AM, Wills M (2004) Tetrahedron Lett 45:843

    Article  CAS  Google Scholar 

  100. Matharu DS, Morris DJ, Kawamoto AM, Clarkson GJ, Wills M (2005) Org Lett 7:5489

    Article  CAS  Google Scholar 

  101. Hamada T, Torii T, Izawa K, Ikariya T (2004) Tetrahedron 60:7411

    Article  CAS  Google Scholar 

  102. Matharu DS, Morris DJ, Clarkson GJ, Wills M (2006) Chem Commun 3232

  103. Echeverria PG, Férard C, Phansavath P, Ratovelomanana-Vidal V (2015) Catal Commun 62:95

    Article  CAS  Google Scholar 

  104. Baiker A (2015) Chem Soc Rev 44:7449

    Article  CAS  Google Scholar 

  105. Boerner A, Krause HW, Kortus K (1988) React Kinet Catal Lett 36:103

    Article  CAS  Google Scholar 

  106. Sarkar SM, Yusoff MM, Rahman ML (2015) J Chin Chem Soc 62:177

    Article  CAS  Google Scholar 

  107. Liu R, Cheng T, Kong L, Chen C, Liu G, Li H (2013) J Catal 307:55

    Article  CAS  Google Scholar 

  108. Bai S, Yang H, Wang P, Gao J, Li B, Yang Q, Li C (2010) Chem Commun 46:8145

    Article  CAS  Google Scholar 

  109. Lettau K, Warsinke A, Katterle M, Danielsson B, Scheller FW (2006) Angew Chem Int Ed 45:6986

    Article  CAS  Google Scholar 

  110. Weng Z, Muratsugu S, Ishiguro N, Ohkoshi S, Tada M (2011) Dalton Trans 40:2338

    Article  CAS  Google Scholar 

  111. Zhang H, Jin R, Yao H, Tang S, Zhuang J, Liu G, Li H (2012) Chem Commun 48:7874

    Article  CAS  Google Scholar 

  112. Gao F, Jin R, Zhang D, Liang Q, Ye Q, Liu G (2013) Green Chem 15:2208

    Article  CAS  Google Scholar 

  113. Xu Y, Cheng T, Long J, Liu K, Qian Q, Gao F, Liu G, Li H (2012) Adv Synth Catal 354:3250

    Article  CAS  Google Scholar 

  114. Long J, Liu G, Cheng T, Yao H, Qian Q, Zhuang J, Gao F, Li H (2013) J Catal 298:41

    Article  CAS  Google Scholar 

  115. Cheng TY, Zhuang JL, Yao H, Zhang HS, Liu GH (2014) Chin Chem Lett 25:613

    Article  CAS  Google Scholar 

  116. Shen Y, Chen Q, Lou LL, Yu K, Ding F, Liu S (2010) Catal Lett 137:104

    Article  CAS  Google Scholar 

  117. Lou LL, Du H, Shen Y, Yu K, Yu W, Chen Q, Liu S (2014) Microporous Mesoporous Mater 187:94

    Article  CAS  Google Scholar 

  118. Wei J, Zhang X, Zhang X, Zhao Y, Li R, Yang Q (2014) ChemCatChem 6:1368

    Article  CAS  Google Scholar 

  119. Zhang X, Zhao Y, Peng J, Yang Q (2015) Green Chem 17:1899

    Article  CAS  Google Scholar 

  120. Liu R, Jin R, Kong L, Wang J, Chen C, Cheng T, Liu G (2013) Chem Asian J 8:3108

    Article  CAS  Google Scholar 

  121. Wang R, Wan J, Ma X, Xu X, Liu L (2013) Dalton Trans 42:6513

    Article  CAS  Google Scholar 

  122. Li X, Wu X, Chen W, Hancock FE, King F, Xiao J (2004) Org Lett 6:3321

    Article  CAS  Google Scholar 

  123. Shan W, Meng F, Wu Y, Mao F, Li X (2011) J Organomet Chem 696:1687

    Article  CAS  Google Scholar 

  124. Zhou Z, Ma Q (2011) Appl Organomet Chem 25:233

    CAS  Google Scholar 

  125. Zammit CM, Wills M (2013) Tetrahedron Asymmetry 24:844

    Article  CAS  Google Scholar 

  126. Sun Q, Jin Y, Zhu L, Wang L, Meng X, Xiao FS (2013) Nano Today 8:342

    Article  CAS  Google Scholar 

  127. Marcos R, Jimeno C, Pericàs MA (2011) Adv Synth Catal 353:1345

    Article  CAS  Google Scholar 

  128. Dimroth J, Keilitz J, Schedler U, Schomäcker R, Haag R (2010) Adv Synth Catal 352:2497

    Article  CAS  Google Scholar 

  129. Elias S, Goren K, Vigalok A (2012) Synlett 23:2619

    Article  CAS  Google Scholar 

  130. Wang W, Wang Q (2010) Chem Commun 46:4616

    Article  CAS  Google Scholar 

  131. Tang S, Jin R, Zhang H, Yao H, Zhuang J, Liu G, Li H (2012) Chem Commun 48:6286

    Article  CAS  Google Scholar 

  132. Michalek F, Lagunas A, Jimeno C, Pericàs MA (2008) J Mater Chem 18:4692

    Article  CAS  Google Scholar 

  133. Gao X, Liu R, Zhang D, Wu M, Cheng T, Liu G (2014) Chem Eur J 20:1515

    Article  CAS  Google Scholar 

  134. Sun Y, Liu G, Gu H, Huang T, Zhang Y, Li H (2011) Chem Commun 47:2583

    Article  CAS  Google Scholar 

  135. Zoabi A, Omar S, Abu-Reziq R (2015) Eur J Inorg Chem 2101

  136. Bianchini C, Farnetti E, Graziani M, Peruzzini M, Polo A (1993) Organometallics 12:3753

    Article  CAS  Google Scholar 

  137. Enthaler S, Erre G, Tse MK, Junge K, Beller M (2006) Tetrahedron Lett 47:8095

    Article  CAS  Google Scholar 

  138. Sui-Seng C, Freutel F, Lough AJ, Morris RH (2008) Angew Chem Int Ed 47:940

    Article  CAS  Google Scholar 

  139. Mikhailine AA, Lough AJ, Morris RH (2009) J Am Chem Soc 131:1394

    Article  CAS  Google Scholar 

  140. Meyer N, Lough AJ, Morris RH (2009) Chem Eur J 15:5605

    Article  CAS  Google Scholar 

  141. Sui-Seng C, Haque FN, Hadzovic A, Pütz AM, Reuss V, Meyer N, Lough AJ, Zimmer-De Iuliis RH, Morris RH (2009) Inorg Chem 48:735

    Article  CAS  Google Scholar 

  142. Sonnenberg JF, Coombs N, Dube PA, Morris RH (2012) J Am Chem Soc 134:5893

    Article  CAS  Google Scholar 

  143. Mikhailine AA, Morris RH (2010) Inorg Chem 49:11039

    Article  CAS  Google Scholar 

  144. Sues PE, Lough AJ, Morris RH (2011) Organometallics 30:4418

    Article  CAS  Google Scholar 

  145. Lagaditis PO, Lough AJ, Morris RH (2010) Inorg Chem 49:10057

    Article  CAS  Google Scholar 

  146. Lagaditis PO, Lough AJ, Morris RM (2011) J Am Chem Soc 133:9662

    Article  CAS  Google Scholar 

  147. Mikhailine AA, Maishan MI, Lough AJ, Morris RH (2012) J Am Chem Soc 134:12266

    Article  CAS  Google Scholar 

  148. Zuo W, Lough AJ, Li YF, Morris RH (2013) Science 342:1080

    Article  CAS  Google Scholar 

  149. Zuo W, Tauer S, Prokopchuk DE, Morris RH (2014) Organometallics 33:5791

    Article  CAS  Google Scholar 

  150. Zuo W, Morris RH (2015) Nat Protoc 10:241

    Article  CAS  Google Scholar 

  151. Brands KMJ, Payack JF, Rosen JD, Nelson TD, Candelario A, Huffman MA, Zhao MM, Li J, Craig B, Song ZJ, Tschaen DM, Hansen K, Devine PN, Pye PJ, Rossen K, Dormer PG, Reamer RA, Welch CJ, Mathre DJ, Tsou NN, McNamara JM, Reider PJ (2003) J Am Chem Soc 125:2129

    Article  CAS  Google Scholar 

  152. Rautenstrauch V, Hoang-Cong X, Churlaud K, Abdur-Rashid K, Morris RH (2003) Chem Eur J 9:4954

    Article  CAS  Google Scholar 

  153. Smith SA, Morris RH (2015) Synthesis 47:1775

    Article  CAS  Google Scholar 

  154. Chen JS, Chen LL, Xing Y, Chen G, Shen WY, Dong ZR (2004) Acta Chimi Sin 62:1745

    CAS  Google Scholar 

  155. Yu S, Shen W, Li Y, Dong Z, Xu Y, Li Q, Zhang J, Gao J (2012) Adv Synth Catal 354:818

    Article  CAS  Google Scholar 

  156. Li Y, Yu S, Wu X, Xiao J, Shen W, Dong Z, Gao J (2014) J Am Chem Soc 136:4031

    Article  CAS  Google Scholar 

  157. Bigler R, Huber R, Mezzetti A (2015) Angew Chem Int Ed 54:5171

    Article  CAS  Google Scholar 

  158. Tanaka K, Katsurada M, Ohno F, Shiga Y, Oda M, Miyagi M, Takehara J, Okano K (2000) J Org Chem 65:432

    Article  CAS  Google Scholar 

  159. Miyagi M, Takehara J, Collet S, Okano K (2000) Org Process Res Dev 4:346

    Article  CAS  Google Scholar 

  160. Naik A, Maji T, Reiser O (2010) Chem Commun 46:4475

    Article  CAS  Google Scholar 

  161. Hopewell JP, Martins JED, Johnson TC, Godfrey J, Wills M (2012) Org Biomol Chem 10:134

    Article  CAS  Google Scholar 

  162. Mohan Kandepi VVK, Cardoso JMS, Peris E, Royo B (2010) Organometallics 29:2777

    Article  CAS  Google Scholar 

  163. Bata P, Notheisz F, Kluson P, Zsigmond A (2014) Appl Organomet Chem 29:45

    Article  CAS  Google Scholar 

  164. Sánchez-Delgado RA, Rosales M, Esteruelas MA, Oro LO (1995) J Mol Catal A 96:231

    Article  Google Scholar 

  165. Schlünken C, Esteruelas MA, Lahoz FJ, Oro LA, Werner H (2004) Eur J Inorg Chem 2477

  166. Carmona Dlamata MP, Viguri F, Dobrinovich I, Lahoz FJ, Oro LA (2002) Adv Synth Catal 344:499

    Article  Google Scholar 

  167. Faller JW, Lavoie AR (2001) Org Lett 3:3703

    Article  CAS  Google Scholar 

  168. Baratta W, Ballico M, Del Zotto A, Siega K, Magnolia S, Rigo P (2008) Chem Eur J 14:2557

    Article  CAS  Google Scholar 

  169. Slade AT, Lensink C, Falshaw A, Clark GR, Wright LJ (2014) Dalton Trans 43:17163

    Article  CAS  Google Scholar 

  170. Coverdale JPC, Sanchez-Cano C, Clarkson GJ, Soni R, Wills M, Sadler P (2015) Chem Eur J 21:8043

    Article  CAS  Google Scholar 

  171. Carmona D, Lahoz FJ, García-Orduña P, Oro LA (2012) Organometallics 31:3333

    Article  CAS  Google Scholar 

  172. Vega E, Lastra E, Gamasa MP (2013) Inorg Chem 52:6193

    Article  CAS  Google Scholar 

  173. Cuervo D, Gamasa MP, Gimeno J (2004) Chem Eur J 10:425

    Article  CAS  Google Scholar 

  174. Le Page MD, James BR (2000) Chem Commun 1647

  175. Phukan P, Sudalai A (2000) Synth Commun 30:2401

    Article  CAS  Google Scholar 

  176. Upadhya TT, Katdare SP, Sabde DP, Ramaswamy V, Sudalai A (1997) Chem Commun 1119

  177. Mohapatra SK, Sonavane SU, Jayaram RV, Selvam P (2002) Org Lett 4:4297

    Article  CAS  Google Scholar 

  178. Alonso F, Riente P, Yus M (2011) Acc Chem Res 44:379

    Article  CAS  Google Scholar 

  179. Shimura K, Shimizu K (2012) Green Chem 14:2983

    Article  CAS  Google Scholar 

  180. Dong ZR, Li YY, Yu SL, Sun GS, Gao JX (2012) Chin Chem Lett 23:533

    Article  CAS  Google Scholar 

  181. Zhang G, Hanson SK (2013) Chem Commun 49:10151

    Article  CAS  Google Scholar 

  182. Neary MC, Parkin G (2015) Chem Sci 6:1859

    Article  CAS  Google Scholar 

  183. Bényei A, Joó F (1990) J Mol Catal 58:151

    Article  Google Scholar 

  184. Wu X, Wang C, Xiao J (2010) Platin Met Rev 54:3

    Article  CAS  Google Scholar 

  185. Wei Y, Wu X, Wang C, Xiao J (2015) Catal Today 247:104

    Article  CAS  Google Scholar 

  186. Li X, Chen W, Hems W, King F, Xiao J (2004) Tetrahedron Lett 45:951

    Article  CAS  Google Scholar 

  187. Wu X, Li X, Hems W, King F, Xiao J (2004) Org Biomol Chem 2:1818

    Article  CAS  Google Scholar 

  188. Wu X, Li X, King F, Xiao J (2005) Angew Chem Int Ed 44:3407

    Article  CAS  Google Scholar 

  189. Wu X, Vinci D, Ikariya T, Xiao J (2005) Chem Commun 41:4447

    Article  CAS  Google Scholar 

  190. Wu X, Liu J, Di Tommaso D, Iggo JA, Catlow CRA, Bacsa J, Xiao J (2008) Chem Eur J 14:7699

    Article  CAS  Google Scholar 

  191. Wills M, Hannedouche J (2002) Curr Opin Drug Discov Dev 5:881

    CAS  Google Scholar 

  192. Wu X, Li X, McConvill M, Saidi O, Xiao J (2006) J Mol Catal A 247:153

    Article  CAS  Google Scholar 

  193. Pavlova A, Meijer EJ (2012) ChemPhysChem 13:3496

    Article  CAS  Google Scholar 

  194. Soltani O, Ariger MA, Vázquez-Villa H, Carreira EM (2010) Org Lett 12:2893

    Article  CAS  Google Scholar 

  195. Vázquez-Villa H, Reber S, Ariger MA, Carreira EM (2011) Angew Chem Int Ed 50:8979

    Article  CAS  Google Scholar 

  196. Ariger MA, Carreira EM (2012) Org Lett 14:4522

    Article  CAS  Google Scholar 

  197. Wei Y, Xue D, Lei Q, Wang C, Xiao J (2013) Green Chem 15:629

    Article  CAS  Google Scholar 

  198. Talwar D, Wu X, Saidi O, Poyatos Salguero N, Xiao J (2014) Chem Eur J 20:12835

    Article  CAS  Google Scholar 

  199. Li L, Wu J, Wong F, Liao J, Zhang H, Lian C, Zhu J, Deng J (2007) Green Chem 9:23

    Article  CAS  Google Scholar 

  200. Tang Y, Li X, Lian C, Zhu J, Deng J (2011) Tetrahedron Asymmetry 22:1530

    Article  CAS  Google Scholar 

  201. Ma Y, Liu H, Chen L, Cui X, Zhu J, Deng J (2003) Org Lett 5:2103

    Article  CAS  Google Scholar 

  202. Li J, Li X, Ma Y, Wu J, Wang F, Xiang J, Zhu J, Wang Q, Deng J (2013) RCS Adv 3:1825

    CAS  Google Scholar 

  203. Kang G, Lin S, Shiwakoti A, Ni B (2014) Catal Commun 57:111

    Article  CAS  Google Scholar 

  204. Zhou Z, Sun Y (2009) Catal Commun 10:1685

    Article  CAS  Google Scholar 

  205. Ahlford K, Lind J, Mäler L, Adolfsson H (2008) Green Chem 10:832

    Article  CAS  Google Scholar 

  206. Zimbron JM, Dauphinais M, Charette AB (2015) Green Chem 17:3255

    Article  CAS  Google Scholar 

  207. Li J, Zhang Y, Han D, Jia G, Gao J, Zhong L, Li C (2008) Green Chem 10:608

    Article  CAS  Google Scholar 

  208. Li J, Tang Y, Wang Q, Li X, Cun L, Zhang X, Zhu J, Li L, Deng J (2012) J Am Chem Soc 134:18522

    Article  CAS  Google Scholar 

  209. Zhou Z, Ma Q, Zhang A, Wu L (2011) Appl Organomet Chem 25:856

    Article  CAS  Google Scholar 

  210. Huo H, Zhou Z, Zhang A, Wu L (2012) Res Chem Intermed 38:261

    Article  CAS  Google Scholar 

  211. Kalsin AM, Peganova TA, Novikov VV, Zhamoytina AI, Gonsalvi L, Peruzzini M (2014) Chem Eur J 20:846

    Article  CAS  Google Scholar 

  212. Romain C, Gaillard S, Elmkaddem MK, Toupet L, Fischmeister C, Thomas CM, Renaud J-L (2010) Organometallics 29:1992

    Article  CAS  Google Scholar 

  213. Azua A, Mata JA, Peris E (2011) Organometallics 30:5532

    Article  CAS  Google Scholar 

  214. Prakash O, Joshi H, Sharma KN, Lal Gupta P, Singh AK (2014) Organometallics 33:3804

    Article  CAS  Google Scholar 

  215. Olivier-Bourbigou H, Magna L, Morvan D (2010) Appl Catal A 373:1

    Article  CAS  Google Scholar 

  216. Berthold H, Schotten T, Hönig H (2002) Synthesis 11:1607

    Google Scholar 

  217. Baán Z, Finta Z, Keglevich G, Hermecz I (2009) Green Chem 11:1937

    Article  CAS  Google Scholar 

  218. Zhou Z, Sun Y, Zhang A (2011) Cent Eur J Chem 9:175

    CAS  Google Scholar 

  219. Strádi A, Molnár M, Szakál P, Dibó G, Gáspár D, Mika LT (2015) RCS Adv 5:72529

    Google Scholar 

  220. Aydemir M, Rafikova K, Kystaubayeva N, Pasa S, Meric N, Ocak YS, Zazybin A, Temel H, Gürbüz N, Özdemir I (2014) Polyhedron 81:245

    Article  CAS  Google Scholar 

  221. Liu X, Chen C, Xiu Y, Chen A, Guo L, Zhang R, Chen J, Hou Z (2015) Catal Commun 67:90

    Article  CAS  Google Scholar 

  222. Vasiloiu M, Gaertner P, Zirbs R, Bica K (2015) Eur J Org Chem 2374

  223. Uchimoto H, Tsuji T, Kawasaki I, Arimitsu K, Yasui H, Yamashita M, Ohta S, Nishide K (2015) Chem Pharm Bull 63:200

    Article  CAS  Google Scholar 

  224. Hems WP, Jackson WP, Nightingale P, Bryant R (2012) Org Process Res Dev 16:461

    Article  CAS  Google Scholar 

  225. Zhou G, Liu X, Liu X, Nie H, Zhang S, Chen W (2013) Adv Synth Catal 355:3575

    Article  CAS  Google Scholar 

  226. Müller M, Orben CM, Schützenmeister N, Schmidt M, Leonov A, Reinscheid UM, Dittrich B, Griesinger C (2013) Angew Chem Int Ed 52:6047

    Article  CAS  Google Scholar 

  227. Hansen KB, Chilenski JR, Desmond R, Devine PN, Grabowski EJJ, Heid R, Kubryk M, Mathre DJ, Varsolona R (2003) Tetrahedron Asymmetry 14:3581

    Article  CAS  Google Scholar 

  228. Blacker AJ, Thompson P (2010) In: Blaser H-U, Federsel H-J (eds) Asymmetric Catalysis on Industrial Scale. Wiley-VHC, Weinheim, p 265

  229. Luo Z, Qin F, Yan S, Li X (2012) Tetrahedron Asymmetry 23:333

    Article  CAS  Google Scholar 

  230. Volpicelli R, Andretto M, Cotarca L, Nardi A, Verzini M (2012) WO2012120086 A1 to ZaCh System SpA

  231. Zhang Q, Ma B-W, Wang Q-Q, Wang X-X, Hu X, Xie M-S, Qu G-R, Guo H-M (2014) Org Lett 16:2014

    Article  CAS  Google Scholar 

  232. Buitrago E, Lundberg H, Andersson H, Ryberg P, Adolfsson H (2012) ChemCatChem 4:2082

    Article  CAS  Google Scholar 

  233. Komiyama M, Itoh T, Takeyasu T (2015) Org Process Res Dev 19:315

    Article  CAS  Google Scholar 

  234. Cortez NA, Aguirre G, Parra-Hake M, Somanathan R (2013) Tetrahedron Asymmetry 24:1297

    Article  CAS  Google Scholar 

  235. Lu C, Luo Z, Huang L, Li X (2011) Tetrahedron Asymmetry 22:722

    Article  CAS  Google Scholar 

  236. Zhang J, Blazecka PG, Bruendl MM, Huang Y (2009) J Org Chem 74:1411

    Article  CAS  Google Scholar 

  237. Bligh CM, Anzalone L, Jung YC, Zhang Y, Nuget WA (2014) J Org Chem 79:3238

    Article  CAS  Google Scholar 

  238. Kumaraswamy G, Ramakrishna G, Naresh P, Jagadeesh B, Balasubramanian S (2009) J Org Chem 74:8468

    Article  CAS  Google Scholar 

  239. Fang Z, Wills M (2014) Org Lett 16:374

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The financial support from the Research Agency of Slovenia through Grant P1-0179 is gratefully acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Franc Požgan.

Additional information

This article is part of the Topical Collection "Hydrogen Transfer Reactions"; edited by Gabriela Guillena, Diego J. Ramón.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Štefane, B., Požgan, F. Metal-Catalysed Transfer Hydrogenation of Ketones. Top Curr Chem (Z) 374, 18 (2016). https://doi.org/10.1007/s41061-016-0015-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s41061-016-0015-5

Keywords

Navigation