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Iron-Catalyzed Reduction and Hydroelementation Reactions

Part of the Topics in Organometallic Chemistry book series (TOPORGAN,volume 50)

Abstract

During the last two decades, iron has proved to be an interesting transition metal which is a highly valuable alternative to classical precious ones for catalyzing organic transformations including the reduction of unsaturated C–C or C–heteroatom bonds. This chapter summarizes the rapid development of iron catalyzed selective reductions of alkene, alkyne, carbonyl and carboxylic derivatives. The emerging topic of hydroboration of alkenes and alkynes is also described.

Keywords

  • Alkenes
  • Alkynes
  • Carbonyl derivatives
  • Carboxylic acid derivatives
  • Hydroboration
  • Hydrogen transfer
  • Hydrogenation
  • Hydrosilylation
  • Iron
  • Reduction

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  • DOI: 10.1007/3418_2015_104
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Scheme 1
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Fig. 1
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Fig. 2
Fig. 3
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Fig. 4
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Scheme 27
Fig. 5
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Scheme 28
Fig. 7
Fig. 8
Scheme 29
Scheme 30
Scheme 31
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Scheme 33
Scheme 34
Scheme 35
Scheme 36
Scheme 37
Scheme 38
Scheme 39
Scheme 40
Scheme 41
Scheme 42
Scheme 43
Scheme 44
Scheme 45
Scheme 46
Scheme 47
Scheme 48
Scheme 49
Scheme 50
Scheme 51

Abbreviations

cat:

Catechol

cod:

1,5-Cyclooctadiene

Cp:

Cyclopentadienyl

dcpe:

1,2-Bisdicyclohexylphosphinoethane

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DFT:

Density functional theory

Dipp:

2,6-Diisopropylphenyl

DMC:

Dimethyl carbonate

DRA:

Direct reductive amination

EDTA-Na2 :

Ethylenediaminetetraacetic acid disodium salt

IMes:

1,3-Bis(2,4,6-trimethylphenyl) imidazole-2-ylidene

IPr:

1,3-Bis(2,6-diisopropylphenyl) imidazole-2-ylidene

MD’M:

[(MeO)2MeSiH]

Mes:

2,4,6-Trimethylphenyl

NHC:

N-Heterocyclic carbene

NPs:

Nanoparticles

pin:

Pinacol

PMHS:

Polymethylhydrosiloxane

t-PBO:

trans-4-Phenyl-but-3-en-2-one

terpy:

2,2′:6′,2″-Terpyridine

TFA:

Trifluoroacetic acid

TMDS:

1,1,3,3-Tetramethyldisiloxane

TMEDA:

N,N,N′,N′-Tetramethylethylenediamine

TMPP:

Tris(2,4,6-trimethoxyphenyl)phosphine

TOF:

Turnover frequency

TON:

Turnover number

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Darcel, C., Sortais, JB. (2015). Iron-Catalyzed Reduction and Hydroelementation Reactions. In: Bauer, E. (eds) Iron Catalysis II. Topics in Organometallic Chemistry, vol 50. Springer, Cham. https://doi.org/10.1007/3418_2015_104

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