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Iron-Catalyzed Carbon–Nitrogen, Carbon–Phosphorus, and Carbon–Sulfur Bond Formation and Cyclization Reactions

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

Abstract

The formation of carbon–heteroatom bonds (C–X bonds with X=N, S, P) upon addition of X-nucleophiles or X-electrophiles to unsaturated alkynes and alkenes, cross-coupling reactions, cycloadditions, tandem or consecutive reactions, or C–H functionalization is an attractive strategy in organic synthesis and is an intensive research area. Many organometallic species, more specifically palladium, nickel, and rhodium complexes, have paved the way to useful synthetic applications in this field. This chapter will cover iron-catalyzed bond-forming reactions between carbon and a heteroatom.

Keywords

  • Iron catalysis
  • C–X bond formation
  • Cross-coupling reactions
  • Cycloaddition
  • C–H functionalization
  • Addition reactions

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Scheme 1
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Fig. 1
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Abbreviations

AIBN:

Azobisisobutyronitrile

BINAP:

2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl

cod:

1,5-Cyclooctadiene

DCIB:

1,2-Dichloroisobutane

DDQ:

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

DMEDA:

N,N′-Dimethylethylenediamine

DMSO:

Dimethyl sulfoxide

dppe:

1,2-Bis(diphenylphosphino)ethane

dppf:

1,1′-Bis(diphenylphosphino)ferrocene

dppp:

1,3-Bis(diphenylphosphino)propane

DTBP:

Di-tert-butyl peroxide

4-F-dppbz:

Bis(4-fluorophenyl)phosphinobenzene

HDA:

Hetero-Diels–Alder reaction

HMDS:

Bis(trimethylsilyl)amine

NBS:

N-Bromosuccinimide

Pc:

Phthalocyaninato

TBHP:

tert-Butyl hydroperoxide, tBuOOH

TEMPO:

(2,2,6,6-Tetramethylpiperidin-1-yl)oxyl

terpy:

Terpyridine ligand

triflate:

OTf, Trifluoromethanesulfonate, CF3SO3

TMSCl:

Trimethylsilyl chloride

TPP:

Tetraphenylporphyrin

TTN:

Total turnover number

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Correspondence to Jean-Luc Renaud .

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Renaud, JL., Gaillard, S. (2015). Iron-Catalyzed Carbon–Nitrogen, Carbon–Phosphorus, and Carbon–Sulfur Bond Formation and Cyclization Reactions. In: Bauer, E. (eds) Iron Catalysis II. Topics in Organometallic Chemistry, vol 50. Springer, Cham. https://doi.org/10.1007/3418_2015_103

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