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Recent Advances in Iridium-Catalysed Transfer Hydrogenation Reactions

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Iridium Catalysts for Organic Reactions

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 69))

Abstract

This review focuses on the contributions of the last 5 years to the application of iridium complexes as homogeneous catalysts in transfer hydrogenation (TH) reactions. The reduction of carbonyls, imines, alkenes and alkynes is considered. The TH of unsaturated alkene-carbonyl substrates and heterocycles is particularly studied. Recent results on the reduction of CO2 are also included. Special attention is paid to THs performed in aqueous medium as well as to the development of TH in biological media. The employ of biomass-derived products as reagents or solvents in TH transformations is also reviewed. Finally, the proposed mechanisms for TH reactions are revised.

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References

  1. Meervein H, Schmidt R (1925) Liebigs Ann Chem 444:221–238

    Google Scholar 

  2. Verley A (1925) Bull Soc Chim Fr 37:537–542

    CAS  Google Scholar 

  3. Ponndorf W (1926) Angew Chem 39:138–143

    CAS  Google Scholar 

  4. Addadh YMY, Henbest HB, Husbands J, Mitchell TRB (1964) Proc Chem Soc Lond:361

    Google Scholar 

  5. Trocha-Grimshaw J, Henbest HB (1967) Chem Commun:544

    Google Scholar 

  6. Sasson Y, Blum J (1971) Tetrahedron Lett 12:2167–2170

    Google Scholar 

  7. Sasson Y, Blum J (1975) J Org Chem 40:1887–1896

    CAS  Google Scholar 

  8. Blum J, Sasson Y, Iflah S (1972) Tetrahedron Lett 13:1015–1018

    Google Scholar 

  9. Chowdhury RL, Bäckvall JE (1991) J Chem Soc Chem Commun:1063–1064

    Google Scholar 

  10. Hashiguchi S, Fujii A, Takehara J, Ikariya T, Noyori R (1995) J Am Chem Soc 117:7562–7563

    CAS  Google Scholar 

  11. Noyori R, Yamakawa M, Hashiguchi S (2001) J Org Chem 66:7931–7944

    CAS  PubMed  Google Scholar 

  12. Li YY, Yu SL, Shen WY, Gao JX (2015) Acc Chem Res 48:2587–2598

    CAS  PubMed  Google Scholar 

  13. Magubane MN, Nyamato GS, Ojwach SO, Munro OQ (2016) RSC Adv 6:65205–65221

    CAS  Google Scholar 

  14. Dubey P, Gupta S, Singh AK (2019) Organometallics 38:944–961

    CAS  Google Scholar 

  15. Shaikh MN (2019) RSC Adv 9:28199–28206

    CAS  Google Scholar 

  16. Foubelo F, Nájera C, Yus M (2015) Tetrahedron Asymmetry 26:769–790

    CAS  Google Scholar 

  17. Chelucci G, Baldino S, Baratta W (2015) Acc Chem Res 48:363–379

    CAS  PubMed  Google Scholar 

  18. Gichumbi JM, Friedrich HB (2018) 866:123–143

    Google Scholar 

  19. Wang F, Lin Xu L, Sun C, Yu L, Xu Q (2018) Appl Organometal Chem 32:e4505

    Google Scholar 

  20. Tang Z, Liu P, Cao H, Bals S, Heeres HJ, Pescarmona PP (2019) ACS Catal 9:9953–9963

    CAS  PubMed  PubMed Central  Google Scholar 

  21. Vilhanová B, van Bokhoven JA, Ranocchiaric M (2017) Adv Synth Catal 359:677–686

    Google Scholar 

  22. Zhao J, Li Q, Zhuang S, Song Y, Morris DJ, Zhou M, Wu Z, Zhang P, Jin R (2018) J Phys Chem Lett 9:7173–7179

    CAS  PubMed  Google Scholar 

  23. Hou SF, Chen JY, Xue M, Jia M, Zhai X, Liao RZ, Tung CH, Wang W (2020) ACS Catal 10:380–390

    CAS  Google Scholar 

  24. Wu W, Seki T, Walker KL, Waymouth RM (2018) Organometallics 37:1428–1431

    CAS  Google Scholar 

  25. Ma F, Chen J, Yang F, Shinde MV, Zhoua Y, Fan B (2017) Org Biomol Chem 15:2359–2362

    CAS  PubMed  Google Scholar 

  26. Xu Y, Long J, Zhao W, Li H, Yang S (2019) Front Chem 7:590

    CAS  PubMed  PubMed Central  Google Scholar 

  27. Mishra AA, Bhanage BM (2019) New J Chem 43:6160–6167

    CAS  Google Scholar 

  28. Cabanillas M, Franco A, Lázaro N, Balu AM, Luque R, Pineda A (2019) Mol Catal 477:110522

    Google Scholar 

  29. Wang F, Planas O, Cornella J (2019) J Am Chem Soc 141:4235–4240

    CAS  PubMed  PubMed Central  Google Scholar 

  30. Bolm C (2009) Nat Chem 1:420–420

    CAS  PubMed  Google Scholar 

  31. Bullock RM (2013) Science 342:1054–1055

    CAS  PubMed  Google Scholar 

  32. Zuo WW, Lough AJ, Li YF, Morris RH (2013) Science 342:1080–1083

    CAS  PubMed  Google Scholar 

  33. Morris RH (2015) Acc Chem Res 48:1494–1502

    CAS  PubMed  Google Scholar 

  34. Zuo W, Morris RH (2015) Nat Protoc 10:241–257

    CAS  PubMed  Google Scholar 

  35. Demmans KZ, Seo CSG, Lough AJ, Morris RH (2017) Chem Sci 8:6531–6541

    CAS  PubMed  PubMed Central  Google Scholar 

  36. Morris RH (2018) Dalton Trans 47:10809–10826

    CAS  PubMed  Google Scholar 

  37. De Luca L, Passera A, Mezzetti A (2019) J Am Chem Soc 141:2545–2255

    PubMed  Google Scholar 

  38. Farrar-Tobar RA, Wozniak B, Savini A, Hinze S, Tin S, de Vries JG (2019) Angew Chem Int Ed 58:1129–1133

    CAS  Google Scholar 

  39. Liang Q, Song D (2020) Chem Soc Rev 49:1209–1232

    CAS  PubMed  Google Scholar 

  40. Jiang BL, Ma SS, Wang ML, Liu DS, Xu BH, Zhang SJ (2019) ChemCatChem 11:1701–1706

    CAS  Google Scholar 

  41. Gao Y, Zhang X, Laishram RD, Chen J, Li K, Zhang K, Zeng G, Fan B (2019) Adv Synth Catal 361:3991–3997

    CAS  Google Scholar 

  42. Bruneau-Voisine A, Wang D, Dorcet V, Roisnel T, Darcel C, Sortais J-B (2017) Org Lett 19:3656–3659

    CAS  PubMed  Google Scholar 

  43. Demmans KZ, Olson ME, Morris RH (2018) Organometallics 37:4608–4618

    CAS  Google Scholar 

  44. Zhou Y-P, Mo Z, Luecke M-P, Driess M (2018) Chem Eur J 24:4780–4784

    CAS  PubMed  Google Scholar 

  45. Wei D, Bruneau-Voisine A, Dubois M, Bastin S, Sortais JB (2019) ChemCatChem 11:5256–5259

    CAS  Google Scholar 

  46. Schneekönig J, Junge K, Beller M (2019) Synlett 30:503–507

    Google Scholar 

  47. Putten RV, Benschop J, Munck VJ, Weber M, Müller C, Filonenko GA, Pidko EA (2019) ChemCatChem 11:5232–5235

    PubMed  PubMed Central  Google Scholar 

  48. Dubey A, Rahaman SMW, Fayzullin RR, Khusnutdinova JR (2019) ChemCatChem 11:3844–3852

    CAS  Google Scholar 

  49. Garduño JA, Flores-Alamo M, García JJ (2019) ChemCatChem 11:5330–5338

    Google Scholar 

  50. Nikita V, Shvydkiy NV, Vyhivskyi O, Nelyubina YV, Perekalin DS (2019) ChemCatChem 11:1602–1605

    Google Scholar 

  51. Ganguli K, Shee S, Panja D, Kundu S (2019) Dalton Trans 48:7358–7366

    CAS  PubMed  Google Scholar 

  52. Vigneswaran V, MacMillan SN, Lacy DC (2019) Organometallics 38:4387–4391

    CAS  Google Scholar 

  53. Zhang C, Hu B, Chen D, Xia H (2019) Organometallics 38:3218–3226

    CAS  Google Scholar 

  54. Zhou L, Liu D, Lan H, Wang X, Zhao C, Ke Z, Hou C (2020) Cat Sci Technol 10:169–179

    CAS  Google Scholar 

  55. Passera A, Mezzetti A (2020) Angew Chem Int Ed 59:187–191

    CAS  Google Scholar 

  56. Uematsu N, Fujii A, Hashiguchi S, Ikariya T, Noyori R (1996) J Am Chem Soc 118:4916–4917

    CAS  Google Scholar 

  57. Wang C, Pettman A, Bacsa J, Xiao J (2010) Angew Chem Int Ed 49:7548–7552

    CAS  Google Scholar 

  58. Liu Z, Romero-Canelón I, Qamar B, Hearn JM, Habtemariam A, Barry NPE, Pizarro AM, Clarkson GJ, Sadler PJ (2014) Angew Chem Int Ed 53:3941–3946

    CAS  Google Scholar 

  59. Wang C, Li C, Wu X, Pettman A, Xiao J (2009) Angew Chem Int Ed 48:6524–6528

    CAS  Google Scholar 

  60. Wang D, Astruc D (2015) Chem Rev 115:6621–6686

    CAS  PubMed  Google Scholar 

  61. Mashima K, Abe T, Tani K (1998) Chem Lett:1199–1200

    Google Scholar 

  62. Bolje A, Hohloch S, van der Meer M, Kosmrlj J, Sarkar B (2015) Chem Eur J 21:6756–6764

    CAS  PubMed  Google Scholar 

  63. Bolje A, Hohloch S, Kosmrlj J, Sarkar B (2016) Dalton Trans 45:15983–15993

    CAS  PubMed  Google Scholar 

  64. Maity R, Hohloch S, Su C-Y, van der Meer M, Sarkar B (2014) Chem Eur J 20:9952–9961

    CAS  PubMed  Google Scholar 

  65. Maity R, van der Meer M, Hohloch S, Sarkar B (2015) Organometallics 34:3090–3096

    CAS  Google Scholar 

  66. Maity R, Mekic A, van der Meer M, Verma A, Sarkar B (2015) Chem Commun 51:15106–15109

    CAS  Google Scholar 

  67. Volpe A, Baldino S, Tubaro C, Baratta W, Basato M, Graiff C (2016) Eur J Inorg Chem:247–251

    Google Scholar 

  68. Müller AL, Bleith T, Roth T, Wadepohl H, Gade LH (2015) Organometallics 34:2326–2342

    Google Scholar 

  69. Gómez-López JL, Chávez D, Parra-Hake M, Royappa AT, Rheingold AL, Grotjahn DB, Miranda-Soto V (2016) Organometallics 35:3148–3153

    Google Scholar 

  70. Vivancos Á, Albrecht M (2017) Organometallics 36:1580–1590

    CAS  Google Scholar 

  71. Pretorius R, Mazloomi Z, Albrecht M (2017) J Organomet Chem 845:196–205

    CAS  Google Scholar 

  72. Navarro M, Smith CA, Albrecht M (2017) Inorg Chem 56:11688–11701

    CAS  PubMed  Google Scholar 

  73. Sato Y, Kayaki Y, Ikariya T (2016) Chem Asian J 11:2924–2931

    CAS  PubMed  Google Scholar 

  74. Holmes J, Pask CM, Willans CE (2016) Dalton Trans 45:15818–15827

    CAS  PubMed  Google Scholar 

  75. Sun M, Campbell J, Kang G, Wang H, Ni B (2016) J Organomet Chem 810:12–14

    CAS  Google Scholar 

  76. Ruff A, Kirby C, Chan BC, O’Connor AR (2016) Organometallics 35:327–335

    CAS  Google Scholar 

  77. Townsend TM, Kirby C, Ruff A, O’Connor AR (2017) J Organomet Chem 843:7–13

    CAS  Google Scholar 

  78. Meriç N, Aydemir M (2016) J Organomet Chem 819:120–128

    Google Scholar 

  79. Ak B, Aydemir M, Durap F, Meriç N, Elma D, Baysal A (2015) Tetrahedron Asymmetry 26:1307–1313

    CAS  Google Scholar 

  80. Durap F, Karakas DE¸ Ak B, Baysal A, Aydemir M (2016) J Organometal Chem 818:92–97

    CAS  Google Scholar 

  81. Baysal A, Karakas DE, Meriç N, Ak B, Aydemir M, Durap F (2017) Trans Met Chem 42:365–372

    CAS  Google Scholar 

  82. Chen HJ, Teo RHX, Li Y, Pullarkat SA, Leung P-H (2018) Organometallics 37:99–106

    CAS  Google Scholar 

  83. Dubey P, Gupta S, Singh AK (2108) Dalton Trans 47:3764–3774

    Google Scholar 

  84. Zhou G, Aboo AH, Robertson CM, Liu R, Li Z, Luzyanin K, Berry NG, Chen W, Xiao J (2018) ACS Catal 8:8020–8026

    CAS  Google Scholar 

  85. Camarena-Díaz JP, Iglesias AL, Chávez D, Aguirre G, Grotjahn DB, Rheingold AL, Parra-Hake M, Miranda-Soto V (2019) Organometallics 38:844–851

    Google Scholar 

  86. Pan H-J, Zhang Y, Shan C, Yu Z, Lan Y, Zhao Y (2016) Angew Chem Int Ed 55:9615–9619

    CAS  Google Scholar 

  87. Wang W-H, Himeda Y, Muckerman JT, Manbeck GF, Fujita E (2015) Chem Rev 115:12936–12973

    CAS  PubMed  Google Scholar 

  88. Sordakis K, Tang C, Vogt LK, Junge H, Dyson PJ, Beller M, Laurenczy G (2018) Chem Rev 118:372–433

    CAS  PubMed  Google Scholar 

  89. Bernskotter WH, Hazari N (2017) Acc Chem Res 50:1049–1058

    Google Scholar 

  90. Klankermayer J, Wesselbaum S, Beydoun K, Leitner W (2016) Angew Chem Int Ed 55:7296–7343

    CAS  Google Scholar 

  91. Goeppert A, Czaun M, Jones J-P, Prakash GKS, Olah GA (2014) Chem Soc Rev 43:7995–8048

    CAS  PubMed  Google Scholar 

  92. Sanz S, Benítez M, Peris E (2010) Organometallics 29:275–277

    CAS  Google Scholar 

  93. Azua A, Sanz S, Peris E (2011) Chem Eur J 17:3963–3967

    CAS  PubMed  Google Scholar 

  94. Kumar A, Semwal S, Choudhury J (2019) ACS Catal 9:2164–2168

    CAS  Google Scholar 

  95. Bar R, Sasson Y (1981) Tetrahedron Lett 22:1709–1710

    CAS  Google Scholar 

  96. Bar R, Sasson Y, Blum J (1984) J Mol Catal 26:327–332

    CAS  Google Scholar 

  97. Bar R, Bar LK, Sasson Y, Blum J (1985) J Mol Catal 33:161–177

    CAS  Google Scholar 

  98. Joó F, Csuhai E, Quinn PJ, Vigh L (1988) J Mol Catal 49:L1–L5

    Google Scholar 

  99. Joó F, Bényei A (1989) J Organomet Chem 363:C19–C21

    Google Scholar 

  100. Bényei A, Joó F (1990) J Mol Catal 58:151–163

    Google Scholar 

  101. Wu X, Xiao J (2007) Chem Commun:2449–2466

    Google Scholar 

  102. Wang C, Wu X, Xiao J (2008) Chem Asian J 3:1750–1770

    CAS  PubMed  Google Scholar 

  103. Wu X, Wang C, Xiao J (2010) Platin Met Rev 54:3–19

    CAS  Google Scholar 

  104. Robertson A, Matsumoto T, Ogo S (2011) Dalton Trans 40:10304–10310

    CAS  PubMed  Google Scholar 

  105. Wei Y, Wub X, Wanga C, Xiao J (2015) Catal Today 247:104–115

    CAS  Google Scholar 

  106. He Y-M, Fan Q-H (2015) ChemCatChem 7:398–400

    CAS  Google Scholar 

  107. Wu X, Wang C, Xiao J (2016) Chem Rec 16:2772–2786

    Google Scholar 

  108. Wang C, Xiao J (2017) Chem Commun 53:3399–3411

    CAS  Google Scholar 

  109. Thangavel S, Friedrich HB, Omondi B (2017) J Mol Caltal A Chem 429:27–42

    CAS  Google Scholar 

  110. Yang Z, Zhu Z, Luo R, Qiu X, Liu J-T, Yang J-K, Tang W (2017) Green Chem 19:3296–3301

    CAS  Google Scholar 

  111. Liu J-T, Yang S, Tang W, Yang Z, Xu J (2018) Green Chem 20:2118–2124

    CAS  Google Scholar 

  112. Liu Q, Wang C, Zhou H, Wang B, Lv J, Cao L, Fu Y (2018) Org Lett 20:971–974

    CAS  PubMed  Google Scholar 

  113. Yang Z, Cheng W, Li Z (2018) Catal Commun 117:38–42

    CAS  Google Scholar 

  114. Davis HJ, Ward TR (2019) ACS Cent Sci 5:1120–1136

    CAS  PubMed  PubMed Central  Google Scholar 

  115. Schwizer F, Okamoto Y, Heinisch T, Gu Y, Pellizzoni MM, Lebrun V, Reuter R, Köhler V, Lewis JC, Ward TR (2018) Chem Rev 118:142–231

    CAS  PubMed  Google Scholar 

  116. Letondor C, Humbert N, Ward TR (2005) Proc Natl Acad Sci U S A 102:4683–4687

    CAS  PubMed  PubMed Central  Google Scholar 

  117. Dürrenberger M, Heinisch T, Wilson YM, Rossel T, Nogueira E, Knörr L, Mutschler A, Kersten K, Zimbron MJ, Pierron J, Schirmer T, Ward TR (2011) Angew Chem Int Ed 50:3026–3029

    Google Scholar 

  118. Hestericov M, Heinisch T, Alonso-Cotchico L, Maréchal J-D, Vidossich P, Ward TR (2018) Angew Chem Int Ed 57:1863–1868

    Google Scholar 

  119. Scott JD, Williams RM (2002) Chem Rev 102:1669–1730

    CAS  PubMed  Google Scholar 

  120. Ward TR (2011) Acc Chem Res 44:47–57

    CAS  PubMed  Google Scholar 

  121. Heinisch T, Ward TR (2016) Acc Chem Res 49:1711–1721

    CAS  PubMed  Google Scholar 

  122. Liang AD, Serrano-Plana J, Peterson RL, Ward TR (2019) Acc Chem Res 52:585–595

    CAS  PubMed  PubMed Central  Google Scholar 

  123. Pellizzoni M, Facchetti G, Gandolfi R, Fusé M, Contini A, Rimoldi I (2016) ChemCatChem 8:1665–1670

    CAS  Google Scholar 

  124. Facchetti G, Rimoldi I (2018) New J Chem 42:18773–18776

    CAS  Google Scholar 

  125. Reetz MT, Wu S, Zheng H, Prasad S (2010) Pure Appl Chem 82:1575–1584

    CAS  Google Scholar 

  126. Denard CA, Ren H, Zhao H (2015) Curr Opin Chem Biol 25:55–64

    CAS  PubMed  Google Scholar 

  127. Quinto T, Häussinger D, Köhler V, Ward TR (2015) Org Biomol Chem 13:357–360

    CAS  PubMed  Google Scholar 

  128. Okamoto Y, Köhler V, Paul CE, Hollmann F, Ward TR (2016) ACS Catal 6:3553–3557

    CAS  Google Scholar 

  129. Okamoto Y, Köhler V, Ward TR (2016) J Am Chem Soc 138:5781–5784

    CAS  PubMed  Google Scholar 

  130. Monnard FW, Nogueira ES, Heinisch T, Schirmerb T, Ward TR (2013) Chem Sci 4:3269–3274

    CAS  Google Scholar 

  131. Monnard FW, Heinisch T, Nogueira ES, Schirmerb T, Ward TR (2011) Chem Commun 47:8238–8240

    CAS  Google Scholar 

  132. Tinberg CE, Khare SD, Dou J, Doyle L, Nelson JW, Schena A, Jankowski W, Kalodimos CG, Johnsson K, Stoddard BL, Baker D (2013) Nature 501:212–218

    CAS  PubMed  PubMed Central  Google Scholar 

  133. Heinisch T, Pellizzoni M, Dürrenberger M, Tinberg CE, Köhler V, Klehr J, Häussinger D, Baker D, Ward TR (2018) J Am Chem Soc 137:10414–10419

    Google Scholar 

  134. Raines DJ, Clarke JE, Blagova EV, Dodson EJ, Wilson KS, Duhme-Klair A-K (2018) Nat Catal 1:680–688

    CAS  Google Scholar 

  135. Lin S-J, Guarente L (2003) Curr Opin Cell Biol 15:241–246

    CAS  PubMed  Google Scholar 

  136. Betanzos-Lara S, Liu Z, Habtemariam A, Pizarro AM, Qamar B, Sadler PJ (2012) Angew Chem Int Ed 51:3897–3900

    CAS  Google Scholar 

  137. Maenaka Y, Suenobu T, Fukuzumi S (2014) J Am Chem Soc 134:367–374

    Google Scholar 

  138. Soldevila-Barreda JJ, Romero-Canelón I, Habtemariam A, Sadler PJ (2015) Nat Commun 6:6582–6590

    CAS  PubMed  Google Scholar 

  139. Ngo AH, Ibáñez M, Do LH (2016) ACS Catal 6:2637–2641

    CAS  Google Scholar 

  140. Bose S, Ngo AH, Do LH (2017) J Am Chem Soc 139:8792–8795

    CAS  PubMed  Google Scholar 

  141. Jang B, Kwon H, Katila P, Lee SJ, Lee H (2016) Adv Drug Deliv Rev 98:113–133

    CAS  PubMed  Google Scholar 

  142. Yang L, Bose S, Ngo AH, Do LH (2017) ChemMedChem 12:292–299

    CAS  PubMed  Google Scholar 

  143. Wang C, Liu J, Tian Z, Tian M, Tian L, Zhao W, Liu Z (2017) Dalton Trans 46:6870–6883

    CAS  PubMed  Google Scholar 

  144. Li JJ, Tian M, Tian Z, Zhang S, Yan C, Shao C, Liu Z (2018) Inorg Chem 57:1705–1716

    CAS  PubMed  Google Scholar 

  145. Li JJ, Guo L, Tian Z, Zhang S, Xu Z, Han Y, Li R, Li Y, Liu Z (2018) Inorg Chem 57:13552–13563

    CAS  PubMed  Google Scholar 

  146. Du Q, Guo L, Tian M, Ge X, Yang Y, Jian X, Xu Z, Tian Z, Liu Z (2018) Organometallics 37:2880–2889

    CAS  Google Scholar 

  147. Du Q, Yang Y, Guo L, Tian M, Ge X, Tian Z, Zhao L, Xu Z, Li J, Liu Z (2019) Dyes Pigments 162:821–830

    CAS  Google Scholar 

  148. Soetens M, Drouet F, Riant O (2017) ChemCatChem 9:929–933

    CAS  Google Scholar 

  149. Stringer T, Melis DR, Smith GS (2019) Dalton Trans:13143–13148

    Google Scholar 

  150. Facchetti G, Pellegrino S, Bucci R, Nava D, Gandolfi R, Christodoulou MS, Rimoldi I (2019) Molecules 2:2771–2779

    Google Scholar 

  151. Campos J, Sharninghausen LS, Manas MG, Crabtree RH (2015) Inorg Chem 54:5079–5084

    CAS  PubMed  Google Scholar 

  152. Jiménez MV, Fernández-Tornos J, Pérez-Torrente JJ, Modrego FJ, García-Orduña P, Oro LA (2015) Organometallics 34:926–940

    Google Scholar 

  153. García N, Jaseer EA, Munarriz J, Sanz Miguel PJ, Polo V, Iglesias M, Oro LA (2015) Eur J Inorg Chem:4388–4395

    Google Scholar 

  154. Ramasamy B, Gangwar MK, Ghosh P (2017) Eur J Inorg Chem:3253–3268

    Google Scholar 

  155. Mazloomi Z, Pretorius R, Pàmies O, Albrecht M, Diéguez M (2017) Inorg Chem 57:11282–11298

    Google Scholar 

  156. Wang H, Jiang T, Xu M-H (2013) J Am Chem Soc 135:971–974

    CAS  PubMed  Google Scholar 

  157. Li Y, Lei M, Yuan W, Meggers E, Lei Gong L (2017) Chem Commun 53:8089–8092

    CAS  Google Scholar 

  158. Albrecht M, van Koten G (2001) Angew Chem Int Ed 40:3650–3781

    Google Scholar 

  159. Peris E, Crabtree RH (2004) Coord Chem Rev 248:2239–2246

    CAS  Google Scholar 

  160. Leis W, Mayera HA, Kaska WC (2008) Coord Cherm Rev 252:1787–1797

    CAS  Google Scholar 

  161. Morales-Morales D (2008) Mini Rev Org Chem 5:141–152

    CAS  Google Scholar 

  162. van der Boom ME, Milstein D (2003) Chem Rev 103:1759–1792

    PubMed  Google Scholar 

  163. Benito-Garagorri D, Kirchner K (2008) Acc Chem Res 41:201–213

    CAS  PubMed  Google Scholar 

  164. Choi J, MacArthur AHR, Brookhart M, Goldman AS (2011) Chem Rev 111:1761–1779

    CAS  PubMed  Google Scholar 

  165. Selander N, Szabó KJ (2011) Chem Rev 111:2048–2076

    CAS  PubMed  Google Scholar 

  166. Gunanathan C, Milstein D (2011) Acc Chem Res 44:588–602

    CAS  PubMed  Google Scholar 

  167. Ito J-I, Nishiyama H (2011) Tetrahedron Lett 55:3133–3145

    Google Scholar 

  168. Gunanathan C, Milstein D (2014) Chem Rev 114:12024–12087

    CAS  PubMed  Google Scholar 

  169. Younus HA, Ahmad N, Su W, Verpoort F (2014) Coord Chem Rev 276:112–152

    CAS  Google Scholar 

  170. Werkmeister S, Neumann J, Junge K, Beller M (2015) Chem Eur J 21:12226–12250

    CAS  PubMed  Google Scholar 

  171. Clarke ZE, Maragh PT, Dasgupta TP, Gusev DG, Lough AJ, Abdur-Rashid K (2006) Organometallics 25:4113–4117

    CAS  Google Scholar 

  172. Paredes P, Díez J, Gamasa P (2008) Organometallics 27:2597–2607

    CAS  Google Scholar 

  173. Bi S, Xie Q, Zhao X, Zhao Y, Kong X (2008) J Organomet Chem 693:633–638

    CAS  Google Scholar 

  174. Azerraf C, Gelman D (2008) Chem Eur J 14:10364–10368

    CAS  PubMed  Google Scholar 

  175. Li Y-H, Zhang Y, Ding X-H (2011) Inorg Chem Commun 14:1306–1310

    CAS  Google Scholar 

  176. Liu W-P, Yuan M-L, Yang X-H, Li K, Xie J-H, Zhou Q-L (2015) Chem Commun 51:6123–6125

    CAS  Google Scholar 

  177. Zhang Y-M, Yuan M-L, Liu W-P, Xie J-H, Zhou Q-L (2018) Org Lett 20:4486–4489

    CAS  PubMed  Google Scholar 

  178. Iturmendi A, García N, Jaseer EA, Munárriz J, Sanz Miguel PJ, Polo V, Iglesias M, Oro LA (2016) Dalton Trans 45:12835–12845

    CAS  PubMed  Google Scholar 

  179. Pandrala M, Resendez A, Malhotra SV (2019) J Catal 378:283–288

    CAS  Google Scholar 

  180. Cohen S, Bilyachenko AN, Gelman D (2019) Eur J Inorg Chem:3203–3209

    Google Scholar 

  181. Wang Y, Huang Z, Leng X, Zhu H, Liu G, Huang Z (2018) J Am Chem Soc 140:4417–4429

    CAS  PubMed  Google Scholar 

  182. Wang Y, Huang Z, Huang Z (2019) Nat Catal 2:529–536

    CAS  Google Scholar 

  183. Zweifel T, Naubron JV, Büttner T, Ott T, Grützmacher H (2008) Angew Chem Int Ed 47:3245–3249

    CAS  Google Scholar 

  184. Reddy AS, Swarmy KCK (2017) Angew Chem Int Ed 56:6984–6988

    Google Scholar 

  185. Chen S, Lu G, Cai C (2015) New J Chem 39:5360–5365

    CAS  Google Scholar 

  186. Wang D, Zhao K, Yang S, Ding Y (2015) Z Anorg Allg Chem 641:400–404

    CAS  Google Scholar 

  187. El-Asaad B, Guicheret B, Métay E, Karamé I, Marc Lemaire M (2016) J Mol Catal A Chem 411:196–202

    CAS  Google Scholar 

  188. Tian C, Gong L, Meggers E (2016) Chem Commun 52:4207–4210

    CAS  Google Scholar 

  189. Ikariya K, Murata K, Noyori R (2006) Org Biomol Chem 4:393–406

    CAS  PubMed  Google Scholar 

  190. Ikariya K, Blacker AJ (2007) Acc Chem Res 40:1300–1308

    CAS  PubMed  Google Scholar 

  191. Landaeta VR, Salazar-La Rosa AD, Rodríguez-Lugo RE (2018) Inorg Chim Acta 470:303–311

    CAS  Google Scholar 

  192. Zhang YM, Li PQ, Liu P (2018) Russ J Coord Chem 44:688–692

    CAS  Google Scholar 

  193. Günnaz S, Gökçe AG, Türkmen H (2018) Dalton Trans 47:17317–17328

    PubMed  Google Scholar 

  194. Zhang D, Iwai T, Sawamura M (2019) Org Lett 21:5867–5872

    CAS  PubMed  Google Scholar 

  195. Yang J, Wang C, Sun Y, Man X, Li J, Sun F (2019) Chem Commun 55:1903–1906

    Google Scholar 

  196. Wang C, Gong S, Liang Z, Sun Y, Cheng R, Yang B, Liu Y, Jinfei Yang J, Sun F (2019) ACS Omega 4:16045–16051

    CAS  PubMed  PubMed Central  Google Scholar 

  197. Farrar-Tobar RA, Tin S, de Vries JG (2018) Selective transfer hydrogenation of α,β-unsaturated carbonyl compounds. In: Dixneuf P, Soulé JF (eds) Organometallics for green catalysis. Topics in organometallic chemistry, vol 63. Springer, Cham

    Google Scholar 

  198. Wang R, Tang Y, Xu M, Meng C, Li F (2018) J Org Chem 83:2274–2281

    CAS  PubMed  Google Scholar 

  199. Luo N, Liao J, Ouyang L, Wen H, Liu J, Tang W, Luo R (2019) Organometallics 38:3025–3011

    CAS  Google Scholar 

  200. Chen S-J, Lu G-P, Chun Cai C (2015) RSC Adv 5:13208–13211

    CAS  Google Scholar 

  201. Ramasamy B, Prakasham AP, Gangwar MK, Ghosh P (2019) Chem Select 4:357–365

    CAS  Google Scholar 

  202. Chrzanowska M, Rozwadowska M (2004) Chem Rev 104:3341–3370

    CAS  PubMed  Google Scholar 

  203. Augustine RL (1995) Heterogeneous catalysis for the synthetic chemist. CRC Press, Boca Raton

    Google Scholar 

  204. Zhou Y-G (2007) Acc Chem Res 40:1357–1366

    CAS  PubMed  Google Scholar 

  205. Wang D-S, Chen Q-A, Lu S-M, Zhou Y-G (2012) Chem Rev 112:2557–2590

    CAS  PubMed  Google Scholar 

  206. Matsunami A, Kayaki Y (2018) Tetrahedron Lett 59:504–513

    CAS  Google Scholar 

  207. Wu J, Tang W, Pettman A, Xiao J (2013) Adv Synth Catal 355:35–40

    CAS  Google Scholar 

  208. Wu J, Wang C, Tang W, Pettman A, Xiao J (2012) Chem Eur J 18:9525–9529

    CAS  PubMed  Google Scholar 

  209. Voutchkova AM, Gnanamgari D, Jakobsche CE, Butler C, Miller SJ, Parr J, Crabtree RH (2008) J Organomet Chem 693:1815–1821

    CAS  Google Scholar 

  210. Frediani P, Rosi L, Cetarini L, Frediani M (2006) Inorg Chim Acta 359:2650–2657

    CAS  Google Scholar 

  211. Fujita K-I, Kitatsuji C, Furukawa S, Yamaguchi R (2004) Tetrahedron Lett 45:3215–3217

    CAS  Google Scholar 

  212. Talwar D, Li HY, Durham E, Xiao J (2015) Chem Eur J 21:5370–5379

    CAS  PubMed  Google Scholar 

  213. Fidalgo J, Ruiz-Castañeda M, García-Herbosa G, Carbayo A, Jalón FA, Rodríguez AM, Manzano BR, Espino G (2018) Inorg Chem 57:14186–14198

    CAS  PubMed  Google Scholar 

  214. Facchetti G, Bucci R, Fusè M, Rimoldi I (2018) Chem Select 3:8797–8800

    CAS  Google Scholar 

  215. Vilhanová BV, Budinská A, Václavík J, Matoušek V, Kuzma M, Červený L (2017) Eur J Org Chem:5131–5134

    Google Scholar 

  216. Xu C, Zhang L, Dong C, Xu J, Pan Y, Li Y, Zhang H, Li H, Yu Z, Xu L (2016) Adv Synth Catal 358:567–572

    CAS  Google Scholar 

  217. Anastas P, Eghbali N (2010) Chem Soc Rev 39:301–312

    CAS  PubMed  Google Scholar 

  218. Omoruyi U, Page S, Hallett J, Miller PW (2016) ChemSusChem 9:2037–2047

    CAS  PubMed  Google Scholar 

  219. Deng J, Wang Y, Pan T, Xu Q, Guo Q-X, Fu Y (2013) ChemSusChem 6:1163–1167

    CAS  PubMed  Google Scholar 

  220. Wang S, Dorcet V, Roisnel T, Bruneau C, Fischmeister C (2017) Organometallics 36:708–713

    CAS  Google Scholar 

  221. Xing R, Qi W, Huber GW (2011) Energy Environ Sci 4:2193–2205

    CAS  Google Scholar 

  222. Karinen R, Kati Vilonen K, Niemel M (2011) ChemSusChem 4:1002–1016

    CAS  PubMed  Google Scholar 

  223. Kabro A, Escudero-Adán EC, Grushin VV, Leeuwen PWNM (2012) Org Lett 14:4014–4017

    CAS  PubMed  Google Scholar 

  224. Constable DJC, Jiménez-González C, Henderson RK (2007) Org Process Res Dev 11:133–137

    CAS  Google Scholar 

  225. Gu Y, Jérôme F (2010) Green Chem 12:1127–1138

    CAS  Google Scholar 

  226. Wolfson A, Dlugy C, Tavor D (2011) Trends Org Chem 15:41–50

    CAS  Google Scholar 

  227. Díaz-Álvarez AE, Cadierno V (2013) Appl Sci 3:55–69

    Google Scholar 

  228. Crabtree RH (2019) ACS Sustain Chem Eng 7:15845–15853

    CAS  Google Scholar 

  229. Azua A, Finn M, Yi H, Dantas AB, Voutchkova-Kostal A (2017) ACS Sustain Chem Eng 5:3963–3972

    CAS  Google Scholar 

  230. Nishina Y (2019) Inorganics 7:114

    CAS  Google Scholar 

  231. Yoshida M, Hirahata R, Inoue T, Shimbayashi T, Fujita K-I (2019) Catalysts 9:503

    Google Scholar 

  232. Mwansa JM, Page MI (2020) Cat Sci Technol 10:590–612

    CAS  Google Scholar 

  233. Cheng-Xing C, Chen H, Li SJ, Zhang T, Qu LB, Lan Y (2020) Coord Chem Rev 412:213251

    Google Scholar 

  234. Samec JSM, Bäckvall JE, Andersson PG, Brandt P (2006) Chem Soc Rev 35:237–248

    CAS  PubMed  Google Scholar 

  235. Noyori R, Ohkuma T (2001) Angew Chem Int Ed 40:40–73, and references therein

    CAS  Google Scholar 

  236. Dub PA, Gordon JC (2016) Dalton Trans 45:6756–6781

    CAS  PubMed  Google Scholar 

  237. Dub PA, Gordon JC (2017) ACS Catal 7:6635–6655

    CAS  Google Scholar 

  238. Dub PA, Gordon JC (2018) Nat Rev Chem 2:396–408

    CAS  Google Scholar 

  239. Handgraaf JW, Reek JNH, Meijer EJ (2003) Organometallics 22:3150–3157

    CAS  Google Scholar 

  240. Chen HYT, Wang C, Wu X, Jiang X, Catlow CRA, Xiao J (2015) Chem Eur J 21:16564–16577

    CAS  PubMed  Google Scholar 

  241. Stirling MJ, Sweeney G, MacRory K, Blacker AJ, Page MI (2016) Org Biomol Chem 14:3614–3622

    CAS  PubMed  Google Scholar 

  242. Demianets I, Cherepakhin V, Maertens A, Lauridsen PJ, Sharada SM, Williams TJ (2020) Polyhedron 182:114508

    CAS  PubMed  PubMed Central  Google Scholar 

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Pilar Lamata, M., Passarelli, V., Carmona, D. (2020). Recent Advances in Iridium-Catalysed Transfer Hydrogenation Reactions. In: Oro, L.A., Claver, C. (eds) Iridium Catalysts for Organic Reactions. Topics in Organometallic Chemistry, vol 69. Springer, Cham. https://doi.org/10.1007/3418_2020_59

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