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Iron-Catalyzed C–C Cross-Couplings Using Organometallics

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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.

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Notes

  1. Some aryl Grignard reagents were also coupled.

  2. Some examples of coupling with aryl Grignard reagents are also reported albeit with moderate yields.

  3. ZnCl2·TMEDA was used as a source of TMEDA.

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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  1. Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231, ESPCI Paris/CNRS/PSL* Research Institute, 10 rue Vauquelin, 75231, Paris Cedex 05, France

    Amandine Guérinot & Janine Cossy

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  1. Amandine Guérinot
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  2. Janine Cossy
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Correspondence to Amandine Guérinot.

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This article is part of the Topical Collection “Ni- and Fe-Based Cross-Coupling Reactions”; edited by “Arkaitz Correa”.

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Guérinot, A., Cossy, J. Iron-Catalyzed C–C Cross-Couplings Using Organometallics. Top Curr Chem (Z) 374, 49 (2016). https://doi.org/10.1007/s41061-016-0047-x

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