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Negishi coupling: an easy progress for C–C bond construction in total synthesis

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Abstract

Negishi cross-coupling reactions were used extensively in total synthesis. The expansion of substrate scope, the development of mild reaction conditions, the advancement of the methods to improve the stereo- and regio-selectivity of carbon–carbon bond formation, the maturity of a large number of sequential processes, and the development of non-toxic reactions signify the importance of Negishi coupling. The following review illustrates a strategic role of this reaction in constructing carbon–carbon bonds in the recent total synthesis of natural products.

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Abbreviations

Ac:

Acetyl

acac:

Acetylacetonate

Bn:

Benzyl

Boc:

\(t\)-Butyloxycarbonyl

CNS:

Central nervous system

COD:

1,5-Cyclooctadiene

Cp:

Cyclopentadienyl

dba:

Dibenzylidenacetone

dppf:

\(1{,}1^{\prime }\)-Bis(diphenylphosphino)ferrocene

glyme:

1,2-Dimethoxyethane

DMA:

Dimethylacetamide

DMF:

Dimethylformamide

DMPU:

\(N{,}N^{\prime }\)-dimethyl-\(N,N^{\prime }\)-trimethyleneurea

DMS \(=\) DPEphos:

Bis(2-diphenylphosphinophenyl)ether

Fmoc:

9-Fluorenylmethoxycarbonyl

HMDS:

Hexamethyldisilazide

IBAO:

Isobutylaluminoxane

LDA:

Lithium diisopropylamide

MOM:

Methoxymethyl

Ni:

Nickle

nmi:

1-Neomenthylindenyl

NMP:

\(N\)-methylpyrrolidone

Pd:

Palladium

PEPPSITM-IPr:

Pyridine-enhanced precatalyst preparation, stabilization and initiation-diisopropylphenylimidazolium derivative

PMB:

\(p\)-Methoxybenzyl

Pybox:

2,6-Bis[(4\(R\))-4-phenyl-2-oxazolinyl] pyridine

SEM:

2-Trimethylsilylethoxymethoxy

TBAF:

Tetra-\(n\)-butylammonium fluoride

TBDPS:

\(t\)-Butyldiphenylsilyl

TBME:

\(tert\)-Butylmethylether

TBS:

\(tert\)-Butyl-dimethylsilyl

tBu-Terpy:

4,\(4^\prime {,}4^{\prime \prime }\)-Tri-\(tert\)-butyl-2,\(2{^\prime }\):\(6^{\prime }\),\(2^{\prime }\)- terpyridine

Tf:

Triflate

tfp:

Tri(2-furyl)phosphane

THF:

Tetrahydrofuran

TIPS:

Triisopropylsilyl

TMS:

Tetramethylsilane

tol:

Tolyl

YS:

Yellow substance

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Acknowledgments

The authors are thankful to the Alzahra Research Council for their support.

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  1. Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran

    Majid M. Heravi, Elaheh Hashemi & Niousha Nazari

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  1. Majid M. Heravi
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Heravi, M.M., Hashemi, E. & Nazari, N. Negishi coupling: an easy progress for C–C bond construction in total synthesis. Mol Divers 18, 441–472 (2014). https://doi.org/10.1007/s11030-014-9510-1

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