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Iron-Catalyzed C–C Cross-Couplings Using Organometallics

  • Amandine GuérinotEmail author
  • Janine Cossy
Review
Part of the following topical collections:
  1. Ni- and Fe-Based Cross-Coupling Reactions

Abstract

Over the last decades, iron-catalyzed cross-couplings have emerged as an important tool for the formation of C–C bonds. A wide variety of alkenyl, aryl, and alkyl (pseudo)halides have been coupled to organometallic reagents, the most currently used being Grignard reagents. Particular attention has been devoted to the development of iron catalysts for the functionalization of alkyl halides that are generally challenging substrates in classical cross-couplings. The high functional group tolerance of iron-catalyzed cross-couplings has encouraged organic chemists to use them in the synthesis of bioactive compounds. Even if some points remain obscure, numerous studies have been carried out to investigate the mechanism of iron-catalyzed cross-coupling and several hypotheses have been proposed.

Keywords

Iron Cross-coupling C–C bond formation Organometallics 

Abbreviations

acac

Acetylacetonate

CPME

Cyclopentyl methyl ether

dbm

Dibenzoylmethide

Dipp

2,6-Diisopropylphenyl

dpm

Dipivaloylmethide

dppbz

1,2-Bis(diphenylphosphino)benzene

dppe

1,2-Bis(diphenylphosphino)ethane

dppp

1,2-Bis(diphenylphosphino)propane

HMTA

Hexamethylenetetramine

IMes

1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene

IPr

1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene

NMI

N-Methylimidazole

NMP

N-Methylpyrrolidinone

OA

Oxidative addition

PEG

Polyethylene glycol

RE

Reductive elimination

SciOPP

Spin-control-intended o-phenylene bis-phosphine

SIPr

1,3-Bis(2,6-di-i-propylphenyl)imidazolidin-2-ylidene

TC

Thiophene carboxylate

THF

Tetrahydrofuran

TM

Transmetalation

TMCD

Tetramethylcyclohexan-1,2-diamine

TMEDA

Tetramethylethanediamine

TMP

Tetramethylpiperidine

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Copyright information

© Springer International Publishing Switzerland 2016

Authors and Affiliations

  1. 1.Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231ESPCI Paris/CNRS/PSL* Research InstituteParis Cedex 05France

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