Exploiting metal-ligand bifunctional reactions in the design of iron asymmetric hydrogenation catalysts

Accounts of Chemical Research

Volumn 48, Issue 5, 2015, Pages 1494-1502

  Morris, Robert H ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84929579823     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00045     Document Type: Article

References (74)

1. Noyori, R. Asymmetric catalysis: Science and opportunities (Nobel lecture) Angew. Chem., Int. Ed. 2002, 41, 2008-2022
2. Clapham, S. E.; Hadzovic, A.; Morris, R. H. Mechanisms of the H2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexes Coord. Chem. Rev. 2004, 248, 2201-2237
3. Zhao, B.; Han, Z.; Ding, K. The N-H functional group in organometallic catalysis Angew. Chem., Int. Ed. 2013, 52, 4744-4788
4. Morris, R. H. Asymmetric hydrogenation, transfer hydrogenation and hydrosilylation of ketones catalyzed by iron complexes Chem. Soc. Rev. 2009, 38, 2282-2291
5. Sues, P. E.; Demmans, K. Z.; Morris, R. H. Rational development of iron catalysts for asymmetric transfer hydrogenation Dalton Trans. 2014, 43, 7650-7667
6. Zuo, W.; Morris, R. H. Synthesis and use of an asymmetric transfer hydrogenation catalyst based on iron(II) Nat. Protoc. 2014, 10, 241-257
7. Sues, P. E.; Cai, K.; McIntosh, D. F.; Morris, R. H. Template effect and ligand substitution methods for the synthesis of iron catalysts: A two part experiment for inorganic chemistry J. Chem. Educ. 2015, 92, 378-381
8. Gopalaiah, K. Chiral iron catalysts for asymmetric synthesis Chem. Rev. 2013, 113, 3248-3296
9. Li, Y.; Yu, S.; Wu, X.; Xiao, J.; Shen, W.; Dong, Z.; Gao, J. Iron catalyzed asymmetric hydrogenation of ketones J. Am. Chem. Soc. 2014, 136, 4031-4039
10. Monfette, S.; Turner, Z. R.; Semproni, S. P.; Chirik, P. J. Enantiopure C-1-symmetric bis(imino)pyridine cobalt complexes for asymmetric alkene hydrogenation J. Am. Chem. Soc. 2012, 134, 4561-4564
11. Friedfeld, M. R.; Shevlin, M.; Hoyt, J. M.; Krska, S. W.; Tudge, M. T.; Chirik, P. J. Cobalt precursors for high-throughput discovery of base metal asymmetric alkene hydrogenation catalysts Science 2013, 342, 1076-1080
12. Hoyt, J. M.; Shevlin, M.; Margulieux, G. W.; Krska, S. W.; Tudge, M. T.; Chirik, P. J. Synthesis and hydrogenation activity of iron dialkyl complexes with chiral bidentate phosphines Organometallics 2014, 33, 5781-5790
13. Casey, C. P.; Guan, H. R. Cyclopentadienone iron alcohol complexes: Synthesis, reactivity, and implications for the mechanism of iron-catalyzed hydrogenation of aldehydes J. Am. Chem. Soc. 2009, 131, 2499-2507
14. Shibasaki, M.; Kanai, M.; Matsunaga, S.; Kumagai, N. Recent progress in asymmetric bifunctional catalysis using multimetallic systems Acc. Chem. Res. 2009, 42, 1117-1127
15. Askevold, B.; Roesky, H. W.; Schneider, S. Learning from the neighbors: Improving homogeneous catalysts with functional ligands motivated by heterogeneous and biocatalysis ChemCatChem 2012, 4, 307-320
16. Dub, P. A.; Ikariya, T. Catalytic reductive transformations of carboxylic and carbonic acid derivatives using molecular hydrogen ACS Catal. 2012, 2, 1718-1741
17. van der Vlugt, J. I. Cooperative catalysis with first-row late transition metals Eur. J. Inorg. Chem. 2012, 363-375
18. Rodríguez-Lugo, R. E.; Trincado, M.; Vogt, M.; Tewes, F.; Santiso-Quinones, G.; Grützmacher, H. A homogeneous transition metal complex for clean hydrogen production from methanol-water mixtures Nat. Chem. 2013, 5, 342-347
19. Gunanathan, C.; Milstein, D. Applications of acceptorless dehydrogenation and related transformations in chemical synthesis Science 2013, 341 1229712
20. Zeng, G. X.; Sakaki, S.; Fujita, K.; Sano, H.; Yamaguchi, R. Efficient catalyst for acceptor less alcohol dehydrogenation: Interplay of theoretical and experimental studies ACS Catal. 2014, 4, 1010-1020
21. Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. Practical enantioselective hydrogenation of aromatic ketones J. Am. Chem. Soc. 1995, 117, 2675-2676
22. Noyori, R.; Ohkuma, T. Asymmetric catalysis by architectural and functional molecular engineering: practical chemo- and stereoselective hydrogenation of ketones Angew. Chem., Int. Ed. 2001, 40, 40-73
23. Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. Asymmetric transfer hydrogenation of α-β-acetylenic ketones J. Am. Chem. Soc. 1997, 119, 8738-8739
24. Mikhailine, A. A.; Maishan, M. I.; Morris, R. H. Asymmetric transfer hydrogenation of ketimines using well-defined iron(II)-based precatalysts containing a PNNP ligand Org. Lett. 2012, 14, 4638-4641
25. Zhou, S. L.; Fleischer, S.; Junge, K.; Beller, M. Cooperative transition-metal and chiral Brønsted acid catalysis: Enantioselective hydrogenation of imines to form amines Angew. Chem., Int. Ed. 2011, 50, 5120-5124
26. Haack, K. J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. The catalyst precursor, catalyst, and intermediate in the Ru(II)-promoted asymmetric hydrogen-transfer between alcohols and ketones Angew. Chem., Int. Ed. 1997, 36, 285-288
27. Noyori, R.; Hashiguchi, S. Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes Acc. Chem. Res. 1997, 30, 97-102
28. Yamakawa, M.; Yamada, I.; Noyori, R. CH/π attraction: The origin of enantioselectivity in transfer hydrogenation of aromatic carbonyl compounds catalyzed by chiral eta(6) arene ruthenium(II) complexes Angew. Chem., Int. Ed. 2001, 40, 2818-2821
29. Schlaf, M.; Lough, A. J.; Morris, R. H. Dihydrogen thiolate vs. hydride thiol: Reactivity of the series of complexes MH(CO)(L)(PPh3)2, M = Ru, Os, L = pyridine-2-thiolate, quinoline-8-thiolate with acid Organometallics 1996, 15, 4423-4436
30. Lough, A. J.; Park, S.; Ramachandran, R.; Morris, R. H. Switching on and off a new intramolecular hydrogen-hydrogen interaction and the heterolytic splitting of dihydrogen. crystal and molecular structure of [Ir{H(SC5H4NH)}2(PCy3)2](BF4).2.7CH2Cl2 J. Am. Chem. Soc. 1994, 116, 8356-8357
31. Abdur-Rashid, K.; Faatz, M.; Lough, A. J.; Morris, R. H. Catalytic cycle for the asymmetric hydrogenation of prochiral ketones to chiral alcohols: Direct hydride and proton transfer from chiral catalysts trans -Ru(H)2(diphosphine)(diamine) to ketones and direct addition of dihydrogen to the resulting hydridoamido complexes J. Am. Chem. Soc. 2001, 123, 7473-7474
32. Abdur-Rashid, K.; Clapham, S. E.; Hadzovic, A.; Harvey, J. N.; Lough, A. J.; Morris, R. H. Mechanism of the hydrogenation of ketones catalyzed by trans -dihydrido(diamine)ruthenium(II) complexes J. Am. Chem. Soc. 2002, 124, 15104-15118
33. Hadzovic, A.; Song, D.; MacLaughlin, C. M.; Morris, R. H. A mechanism displaying autocatalysis: The hydrogenation of acetophenone catalyzed by RuH(S binap)(app) where app is the amido ligand derived from 2-amino-2-(2-pyridyl)-propane Organometallics 2007, 26, 5987-5999
34. Sandoval, C. A.; Ohkuma, T.; Muniz, K.; Noyori, R. Mechanism of asymmetric hydrogenation of ketones catalyzed by BINAP/1,2-diamine-ruthenium(II) complexes J. Am. Chem. Soc. 2003, 125, 13490-13503
35. Lindner, E.; Mayer, H. A.; Warad, I.; Eichele, K. Supported organometallic complexes-Part XXXV. Synthesis, characterization, and catalytic application of a new family of diamine(diphosphine)ruthenium(II) complexes J. Organomet. Chem. 2003, 665, 176-185
36. Mikami, K.; Korenaga, T.; Yusa, Y.; Yamanaka, M. Asymmetric activation/deactivation of racemic Ru catalysts for highly enantioselective hydrogenation irrespective of ketonic substrates: Molecular design of dimethylbinaphthylamine for enantiomeric catalysts discrimination Adv. Syn. Catal. 2003, 345, 246-254
37. Boubekeur, L.; Ulmer, S.; Ricard, L.; Mezailles, N.; LeFloch, P. A stable hydrido amido ruthenium complex bearing a tridentate iminophosphorane-phosphine-amine ligand Organometallics 2006, 25, 315-317
38. Jeffery, J. C.; Rauchfuss, T. B.; Tucker, P. A. Metal complexes of diiminodiphosphines. Structural and reactivity patterns Inorg. Chem. 1980, 19, 3306-3315
39. Gao, J. X.; Ikariya, T.; Noyori, R. A ruthenium(II) complex with a C-2-symmetrical diphosphine/diamine tetradentate ligand for asymmetric transfer hydrogenation of aromatic ketones Organometallics 1996, 15, 1087-1089
40. Rautenstrauch, V.; Hoang-Cong, X.; Churlaud, R.; Abdur-Rashid, K.; Morris, R. H. Hydrogenation versus transfer hydrogenation of ketones: Two established ruthenium systems catalyze both Chem.-Eur. J. 2003, 9, 4954-4967
41. Chen, J.-S.; Chen, L.-L.; Xing, Y.; Chen, G.; Shen, W.-Y.; Dong, Z.-R.; Li, Y.-Y.; Gao, J.-X. Asymmetric transfer hydrogenation of ketones catalyzed by chiral carbonyl iron systems Huaxue Xuebao 2004, 62, 1745-1750
42. Sui-Seng, C.; Freutel, F.; Lough, A. J.; Morris, R. H. Highly efficient catalyst systems using iron complexes with a tetradentate PNNP ligand for the asymmetric hydrogenation of polar bonds Angew. Chem., Int. Ed. 2008, 47, 940-943
43. Meyer, N.; Lough, A. J.; Morris, R. H. Iron(II) complexes for the efficient catalytic asymmetric transfer hydrogenation of ketones Chem.-Eur. J. 2009, 15, 5605-5610
44. Sui-Seng, C.; Haque, F. N.; Hadzovic, A.; Pütz, A.-M.; Reuss, V.; Meyer, N.; Lough, A. J.; Iuliis, M. Z.-D.; Morris, R. H. Synthesis and characterization of iron(II) complexes with tetradentate diiminodiphosphine or diaminodiphosphine ligands as precatalysts for the hydrogenation of acetophenone Inorg. Chem. 2009, 48, 735-743
45. Sonnenberg, J. F.; Morris, R. H. Evidence for iron nanoparticles catalyzing the rapid dehydrogenation of ammonia-borane ACS Catal. 2013, 3, 1092-1102
46. Mikhailine, A. A.; Kim, E.; Dingels, C.; Lough, A. J.; Morris, R. H. Template syntheses of iron(II) complexes containing chiral P-N-N-P and P-N-N ligands Inorg. Chem. 2008, 47, 6587-6589
47. Mikhailine, A. A.; Lough, A. J.; Morris, R. H. Efficient asymmetric transfer hydrogenation of ketones catalyzed by an iron complex containing a P-N-N-P tetradentate ligand formed by template synthesis J. Am. Chem. Soc. 2009, 131, 1394-1395
48. Lagaditis, P. O.; Mikhailine, A. A.; Lough, A. J.; Morris, R. H. Template synthesis of iron(II) complexes containing tridentate P-N-S, P-N-P, P-N-N and tetradentate P-N-N-P Ligands Inorg. Chem. 2010, 49, 1094-1102
49. Sues, P. E.; Lough, A. J.; Morris, R. H. Stereoelectronic factors in iron catalysis: Synthesis and characterization of aryl-substituted iron(II) carbonyl P-N-N-P complexes and their use in the asymmetric transfer hydrogenation of ketones Organometallics 2011, 30, 4418-4431
50. Mikhailine, A. A.; Maishan, M. I.; Lough, A. J.; Morris, R. H. The mechanism of efficient asymmetric transfer hydrogenation of acetophenone using an iron(II) complex containing an (S, S)-Ph2PCH2CH=NCHPhCHPhN=CHCH2PPh2 ligand: Partial ligand reduction is the key J. Am. Chem. Soc. 2012, 134, 12266-12280
51. Lagaditis, P. O.; Lough, A. J.; Morris, R. H. Low-valent ene-amido iron complexes for the asymmetric transfer hydrogenation of acetophenone without base J. Am. Chem. Soc. 2011, 133, 9662-9665
52. Prokopchuk, D. E.; Morris, R. H. Inner-sphere activation, outer-sphere catalysis: Theoretical study on the mechanism of transfer hydrogenation of ketones using iron(II) PNNP eneamido complexes Organometallics 2012, 31, 7375-7385
53. Zuo, W. W.; Lough, A. J.; Li, Y. F.; Morris, R. H. Amine(imine)diphosphine iron catalysts for asymmetric transfer hydrogenation of ketones and imines Science 2013, 342, 1080-1083
54. Zuo, W.; Tauer, S.; Prokopchuk, D. E.; Morris, R. H. Iron catalysts containing amine(imine)diphosphine P-NH-N-P ligands catalyze both the asymmetric hydrogenation and asymmetric transfer hydrogenation of ketones Organometallics 2014, 33, 5791-5801
55. Smith, S. A. M.; Morris, R. H. An unsymmetrical iron complex for the asymmetric transfer hydrogenation of ketones Synthesis 2015, 10.1055/s-0034-1380147
56. Lagaditis, P. O.; Sues, P. E.; Lough, A. J.; Morris, R. H. Exploring the decomposition pathways of iron asymmetric transfer hydrogenation catalysts Dalton Trans. 2014, 10.1039/C1034DT02799J
57. Chen, Y.; Tang, Y. H.; Lei, M. A comparative study on the hydrogenation of ketones catalyzed by diphosphine-diamine transition metal complexes using DFT method Dalton Trans. 2009, 2359-2364
58. O, W. W. N.; Lough, A. J.; Morris, R. H. Factors favoring efficient bifunctional catalysis. A study of a ruthenium(II) hydrogenation catalyst containing an N-heterocyclic carbene with a primary amine donor Organometallics 2012, 31, 2137-2151
59. Langer, R.; Iron, M. A.; Konstantinovski, L.; Diskin-Posner, Y.; Leitus, G.; Ben-David, Y.; Milstein, D. Iron borohydride pincer complexes for the efficient hydrogenation of ketones under mild, base-free conditions: Synthesis and mechanistic insight Chem.-Eur. J. 2012, 18, 7196-7209
60. Bornschein, C.; Werkmeister, S.; Wendt, B.; Jiao, H.; Alberico, E.; Baumann, W.; Junge, H.; Junge, K.; Beller, M. Mild and selective hydrogenation of aromatic and aliphatic (di)nitriles with a well-defined iron pincer complex Nat. Commun. 2014, 5 4111 10.1038/ncomms5111
61. Chakraborty, S.; Dai, H.; Bhattacharya, P.; Fairweather, N. T.; Gibson, M. S.; Krause, J. A.; Guan, H. Iron-based catalysts for the hydrogenation of esters to alcohols J. Am. Chem. Soc. 2014, 136, 7869-7872
62. Chakraborty, S.; Lagaditis, P. O.; Förster, M.; Bielinski, E. A.; Hazari, N.; Holthausen, M. C.; Jones, W. D.; Schneider, S. Well-defined iron catalysts for the acceptorless reversible dehydrogenation-hydrogenation of alcohols and ketones ACS Catal. 2014, 4, 3994-4003
63. Chakraborty, S.; Brennessel, W. W.; Jones, W. D. A molecular iron catalyst for the acceptorless dehydrogenation and hydrogenation of N-heterocycles J. Am. Chem. Soc. 2014, 136, 8564-8567
64. Alberico, E.; Sponholz, P.; Cordes, C.; Nielsen, M.; Drexler, H. J.; Baumann, W.; Junge, H.; Beller, M. Selective hydrogen production from methanol with a defined iron pincer catalyst under mild conditions Angew. Chem., Int. Ed. 2013, 52, 14162-14166
65. Bielinski, E. A.; Lagaditis, P. O.; Zhang, Y. Y.; Mercado, B. Q.; Wurtele, C.; Bernskoetter, W. H.; Hazari, N.; Schneider, S. Lewis acid-assisted formic acid dehydrogenation using a pincer-supported iron catalyst J. Am. Chem. Soc. 2014, 136, 10234-10237
66. Lagaditis, P. O.; Sues, P. E.; Sonnenberg, J. F.; Wan, K. Y.; Lough, A. J.; Morris, R. H. Iron(II) complexes containing unsymmetrical P-N-P′ pincer ligands for the catalytic asymmetric hydrogenation of ketones and imines J. Am. Chem. Soc. 2014, 136, 1367-1380
67. Morris, R. H.; Sawyer, J. F.; Shiralian, M.; Zubkowski, J. Two molecular hydrogen complexes: trans -[M(η2-H2)(H)(PPh2CH2CH2PPh2)2]BF4 (M = Fe, Ru). The crystal structure determination of the iron complex J. Am. Chem. Soc. 1985, 107, 5581-5582
68. Morris, R. H. Estimating the acidity of transition metal hydride and dihydrogen complexes by adding ligand acidity constants J. Am. Chem. Soc. 2014, 136, 1948-1959
69. Abdur-Rashid, K.; Fong, T. P.; Greaves, B.; Gusev, D. G.; Hinman, J. G.; Landau, S. E.; Lough, A. J.; Morris, R. H. An acidity scale in THF for phosphorus-containing compounds including metal hydrides and dihydrogen complexes: Toward the unification of acidity scales J. Am. Chem. Soc. 2000, 122, 9155-9171
70. Fong, T. P.; Forde, C. E.; Lough, A. J.; Morris, R. H.; Rigo, P.; Rocchini, E.; Stephan, T. Synthesis of the acidic dihydrogen complexes trans -[M(H2)(CN)L2]+ and trans -[M(H2)(CNH)L2]2+ where M = Fe, Ru, Os and L = dppm, dppe, dppp, depe, and dihydrogen substitution by the trifluoromethylsulfonate anion to give trans -[Ru(OTf)(CN)L2] or trans -[Ru(OTf)(CNH)L2]OTf J. Chem. Soc., Dalton Trans. 1999, 4475-4486
71. Forde, C. E.; Landau, S. E.; Morris, R. H. Dicationic iron(II) complexes with dihydrogen trans to p-acid ligands: trans-[Fe(η2-H2)(L)(dppe)2]+2 (L = CO, CNH). Is there Fe-H2 π-backbonding? J. Chem. Soc., Dalton Trans. 1997, 1663-1664
72. Amrhein, P. I.; Drouin, S. D.; Forde, C. E.; Lough, A. J.; Morris, R. H. Ancillary ligand control of reactivity. Protonation at hydride versus cyanide in trans -[FeH(CN)(R2PCH2CH2PR2)2] (R = Et, Ph and p -tolyl) and X-ray crystal structure determination of trans -[FeH(CNH)(R2PCH2CH2PR2)2](BF4) R = p -tolyl J. Chem. Soc., Chem. Commun. 1996, 1665-1666
73. Forde, C. E.; Morris, R. H. Transition metal complexes as models of the active sites of hydrogenases. In Electron Transfer in Chemistry; Balzani, V., Eds.; Wiley VCH: Weinheim, Germany, 2001; Vol. 2, Section 2, pp 905-926.
74. Lubitz, W.; Ogata, H.; Rüdiger, O.; Reijerse, E. Hydrogenases Chem. Rev. 2014, 114, 4081-4148