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Iron-promoted Reduction Reactions

Organoiron Compounds (2013)

  1. Hideo Nagashima1,
  2. Yusuke Sunada2,
  3. Takashi Nishikata3,
  4. Arada Chaiyanurakkul4

Published Online: 28 APR 2014

DOI: 10.1002/9780470682531.pat0659

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Nagashima, H., Sunada, Y., Nishikata, T. and Chaiyanurakkul, A. 2014. Iron-promoted Reduction Reactions. Patai's Chemistry of Functional Groups. 1–54.

Author Information

  1. 1

    Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga, Fukuoka 816-8580, Japan

  2. 2

    Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga, Fukuoka 816-8580, Japan

  3. 3

    Graduate School of Science and Engineering, Yamaguchi University, Yamaguchi, 755-8611, Japan

  4. 4

    Department of Chemistry, Faculty of Science, Mahidol University, Ratchathewi, Bangkok 10400, Thailand

Publication History

  1. Published Online: 28 APR 2014

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Abstract

Iron-promoted reduction reactions are described from the standpoint of the catalyst design. Catalysis of three well-defined precatalysts is the first topic; iron complexes having PNNP ligands, Shvo-type complexes, and pincer compounds are active towards catalytic hydrogenation and transfer hydrogenation of ketones. The reduction mechanisms are in line with the concept of Noyori's metal-ligand bifunctional catalysis, in which the ligand plays a key role in the hydrogenation of the carbonyl function. The redox-active ligands in iron-catalyzed hydrogenation and hydrosilylation of alkenes and alkynes provide other important aspects contributing to the catalyst design. In particular, redox properties of bis(imino)pyridine ligands assist the activation of H–H and H–Si bonds in molecular hydrogen and organohydrosilanes leading to efficient hydrogenation and hydrosilylation of alkenes. Reduction reactions mediated by iron compounds, which include catalytic hydrogenation, transfer hydrogenation, and hydrosilylation, are overviewed from organic synthesis, which is promoted by a mixture of iron salts and ligands, ill-defined catalyst precursors, and nanoparticles. From these, the possible catalyst design of iron is discussed.

Keywords:

  • hydrogenation;
  • transfer hydrogenation;
  • hydrosilylation;
  • metal-ligand bifunctional catalysis;
  • redox-active ligands;
  • non-innocent ligands

Featured Compounds

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  1. 1 - 102
Compound 24
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 25
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 8
Molecular Weight:881.757
Molecular Formula:C55H45FeN3OP2
InChIKey:ZNAQVZODHLJWHU-RWUWQGLCSA-N
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Compound 14a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 47
Molecular Weight:286.061
Molecular Formula:C13H10FeO4
InChIKey:BVYZFTVCCNDAIM-YZNHWISSSA-N
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Compound 77
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound sat-A
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 76
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 31-Ru
Molecular Weight:465.61
Molecular Formula:C17H24O5RuSi2
InChIKey:RQLDIUSJLIENGL-UHFFFAOYSA-N
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Compound 32-Ru
Molecular Weight:465.61
Molecular Formula:C17H24O5RuSi2
InChIKey:RQLDIUSJLIENGL-UHFFFAOYSA-N
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Compound 18
Molecular Weight:504.202
Molecular Formula:C20H36BrFeNOP2
InChIKey:HZHDGAAEJFCOGL-UHFFFAOYSA-M
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Compound 83
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 42
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 11a
Molecular Weight:499.143
Molecular Formula:C19H29BrFeN2OP2
InChIKey:DGJSWNKDDSKWPJ-YWIWLAJFSA-M
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Compound 63
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 44
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 9c
Molecular Weight:796.471
Molecular Formula:C43H38BrFeN2OP2
InChIKey:JNJXCVBTVIFBEH-VCVVOJJCSA-M
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Compound 38
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 66
Molecular Weight:934.734
Molecular Formula:C50H54Fe2N12
InChIKey:IBEMJGUMBFZKRT-SWVSAKQBSA-N
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Compound 6
Molecular Weight:796.697
Molecular Formula:C48H46FeN4P2
InChIKey:HBQCTEGCEODOTG-HKROKSSFSA-N
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Compound 75
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 55
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 56
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 27a
Molecular Weight:670.6779
Molecular Formula:C42H42P4
InChIKey:TVLNGWSWPKIYAO-UHFFFAOYSA-N
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Compound 69
Molecular Weight:611.681
Molecular Formula:C37H53FeN3O
InChIKey:OZPMLLNUFHHGFW-GSWKODDSSA-N
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Compound 40
Molecular Weight:531.66
Molecular Formula:C25H45FeN3O2Si2
InChIKey:TWBWOAQMCIHODV-OLVQSPPGSA-N
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Compound 70
Molecular Weight:425.31
Molecular Formula:C19H37FeN3P2
InChIKey:VPXVWRKQUOHEFJ-UHFFFAOYSA-N
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Compound 35
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 72
Molecular Weight:690.759
Molecular Formula:C45H52FeN3
InChIKey:QCMIGAIKRZLFIH-GSWKODDSSA-N
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Compound 39
Molecular Weight:416.6413
Molecular Formula:C29H40N2
InChIKey:FKEPBXIZCNTSMY-VAFAGLDHSA-N
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Compound 78
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 31-Fe
Molecular Weight:420.385
Molecular Formula:C17H24FeO5Si2
InChIKey:KBIKXAMHFGXVMG-UHFFFAOYSA-N
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Compound 32-Fe
Molecular Weight:420.385
Molecular Formula:C17H24FeO5Si2
InChIKey:KBIKXAMHFGXVMG-UHFFFAOYSA-N
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Compound 17-Fe
Molecular Weight:498.54
Molecular Formula:C24H34FeO4Si2
InChIKey:LIMJWUVJCACWCB-UHFFFAOYSA-N
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Compound 46
Molecular Weight:1301.528
Molecular Formula:C34H30Fe7N4O26
InChIKey:VVYFJMCGLZDEPO-UHFFFAOYSA-N
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Compound 9a
Molecular Weight:852.577
Molecular Formula:C47H46BrFeN2OP2
InChIKey:MQNNZBGOLOZYRK-PHGFFVTQSA-M
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Compound 33
Molecular Weight:662.7811
Molecular Formula:C44H44N2P2
InChIKey:OBHPYVNBXWUKNY-COCZKOEFSA-N
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Compound 16-Ru
Molecular Weight:425.59
Molecular Formula:C15H23O4RuSi2
InChIKey:PROWUKVALQUHMS-UHFFFAOYSA-N
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Compound 41
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 34
Molecular Weight:792.9277
Molecular Formula:C52H50N4P2
InChIKey:NHBYGVLDKOZOJJ-XRDANJPLSA-N
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Compound 22
Molecular Weight:425.306
Molecular Formula:C20H37FeNOP2
InChIKey:YDGUXTFRQWEGNK-UHFFFAOYSA-N
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Compound 23
Molecular Weight:425.306
Molecular Formula:C20H37FeNOP2
InChIKey:YDGUXTFRQWEGNK-UHFFFAOYSA-N
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Compound 58
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 11
Molecular Weight:500.15
Molecular Formula:C19H30BrFeN2OP2
InChIKey:YHVMCVKJPIJWEG-SKTPHEQHSA-M
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Compound 14b
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 13
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 3-Ru
Molecular Weight:1094
Molecular Formula:C66H65BP4Ru
InChIKey:MVJOKQOMVNMTIQ-UHFFFAOYSA-N
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Compound 20
Molecular Weight:439.141
Molecular Formula:C20H38BFeNOP2
InChIKey:SHMCTCYNUFJQSH-UHFFFAOYSA-N
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Compound 43
Molecular Weight:435.05
Molecular Formula:C16H15BrFeN2O4
InChIKey:SKBPAGNOFURKER-IJBXMQGASA-M
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Compound 3-Fe
Molecular Weight:1048.773
Molecular Formula:C66H65BFeP4
InChIKey:IPSMYZCHJGAMIU-UHFFFAOYSA-N
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Compound 36
Molecular Weight:397.469
Molecular Formula:C25H23N3O2
InChIKey:ZBONTXCYJLVGLR-SFTDATJTSA-N
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Compound 21
Molecular Weight:411.131
Molecular Formula:C19H38BFeNP2
InChIKey:QGZQTOPDLXKAMX-UHFFFAOYSA-N
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Compound unsat-A
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 57
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 59
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 12
Molecular Weight:753.028
Molecular Formula:C43H39ClFeN2OP2
InChIKey:RGEFBKSSIIYSEA-FFXNUSLHSA-M
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Compound 79
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 27b
Molecular Weight:814.8063
Molecular Formula:C54H42P4
InChIKey:RXLPLNLIQIQVDH-UHFFFAOYSA-N
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Compound 71
Molecular Weight:531.507
Molecular Formula:C25H43FeN3P2Si
InChIKey:GACSPNCFDYMHBA-UHFFFAOYSA-N
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Compound 49
Molecular Weight:755.544
Molecular Formula:C42H42FeN2P4
InChIKey:LKKVTGAFZLTQFX-UHFFFAOYSA-N
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Compound 3
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 81
Molecular Weight:567.097
Molecular Formula:C24H21Br2FeN3
InChIKey:RXEJJZCLULMWLG-UHFFFAOYSA-L
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Compound 7
Molecular Weight:783.655
Molecular Formula:C47H43FeN3OP2
InChIKey:JYFMLYXVXJWOHE-HKROKSSFSA-N
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Compound 15-Ru
Molecular Weight:437.64
Molecular Formula:C17H27O3RuSi2
InChIKey:DFFZFZWEHDJXSM-UHFFFAOYSA-N
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Compound 10(Cl)
Molecular Weight:409.669
Molecular Formula:C15H30ClFeN2OP2
InChIKey:Not Available
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Compound 4
Molecular Weight:834.76
Molecular Formula:C44H44Cl2N2P2Ru
InChIKey:FUMVZHYGXIVLOY-LRUAKEPISA-L
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Compound 60
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 73
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 82
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 54
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 9
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 5
Molecular Weight:830.73
Molecular Formula:C44H40Cl2N2P2Ru
InChIKey:CJIBSIJSJOWYMO-OJRPGWEWSA-L
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Compound 28b
Molecular Weight:525.422
Molecular Formula:C25H45FeNO3P2
InChIKey:COBDHIXQLLLRTC-UHFFFAOYSA-M
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Compound 9b
Molecular Weight:908.683
Molecular Formula:C51H54BrFeN2OP2
InChIKey:NMMRNZWEYIZXPX-XTDCHYAFSA-M
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Compound 30
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 53
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 50
Molecular Weight:755.583
Molecular Formula:C44H46FeP4
InChIKey:IRWBIBJAJNLWAJ-UHFFFAOYSA-N
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Compound 19
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 26
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 3-Os
Molecular Weight:1183.16
Molecular Formula:C66H65BOsP4
InChIKey:MDWLTXSNZJXGON-UHFFFAOYSA-N
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Compound 62
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 74
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound sat-K
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 37
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 68
Molecular Weight:689.713
Molecular Formula:C43H47FeN5
InChIKey:MAXGSJPJGANJGR-YYWPWUNESA-N
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Compound 61
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 15-Fe
Molecular Weight:392.418
Molecular Formula:C17H27FeO3Si2
InChIKey:SOJBHSHALNCIOI-UHFFFAOYSA-N
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Compound 17-Ru
Molecular Weight:543.77
Molecular Formula:C24H34O4RuSi2
InChIKey:GUJWBVCTRQBTRV-UHFFFAOYSA-N
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Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 61
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 28a
Molecular Weight:481.413
Molecular Formula:C24H45FeNOP2
InChIKey:PNBPBDLQACMZEV-UHFFFAOYSA-N
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Compound 10(Br)
Molecular Weight:452.107
Molecular Formula:C15H30BrFeN2OP2
InChIKey:RKEYOPUEUYMRNB-KAFKVMRASA-M
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Compound 65
Molecular Weight:563.597
Molecular Formula:C35H45FeN3
InChIKey:IGQBMAIEIFNZLY-YFGPBBSXSA-N
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Compound 51
Molecular Weight:755.583
Molecular Formula:C44H47FeP4
InChIKey:NLIGGVARCBHIIP-UHFFFAOYSA-N
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Compound 80
Molecular Weight:463.544
Molecular Formula:C23H33FeN3Si2
InChIKey:IDLDREIOODQACR-UHFFFAOYSA-N
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Compound 48
Molecular Weight:248.056
Molecular Formula:C11H12FeO3
InChIKey:GZMATHFPPBUXMJ-SUESZSCISA-N
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Compound 64
Molecular Weight:715.789
Molecular Formula:C47H53FeN3
InChIKey:FUZWJUNZMINCTK-DGOWAXEKSA-N
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Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 67
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 16-Fe
Molecular Weight:380.365
Molecular Formula:C15H23FeO4Si2
InChIKey:PFOASLOFAYOCCX-UHFFFAOYSA-N
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Compound 45
Molecular Weight:651.47
Molecular Formula:C19H8O7Ru3
InChIKey:FWWMRPOXGLAILM-UHFFFAOYSA-N
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Compound 29
Molecular Weight:752.9589
Molecular Formula:C50H57O4P
InChIKey:AGQAQYPGJDBIQR-UHFFFAOYSA-N
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