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Organometallic Approaches to Carbon–Sulfur Bond Formation

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C-X Bond Formation

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 31))

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Abbreviations

%:

Mol %

Acac:

Acetylacetonate

AcOH:

Acetic acid

atm:

Atmosphere

BINAM:

1,1′-binaphthyl-2,2′-diamine

±BINAP:

Racemic 2,2′-bis(diphenylphosphino)-1,1′-binapthyl

[bmim][OTf]:

1-butyl-3-methylimidazolium triflate

Bn:

Benzyl

Bu:

Butyl

C–S:

Carbon–sulfur

CH3CN:

Acetonitrile

cod:

Cyclooctadiene

Conv.:

Conversion

COX-2:

Cyclooxygenase-2

CuI–bipy:

Copper(I) iodide–bipyridine complex

CuMeSal:

Copper(I) 3-methylsalicylate

Cy:

Cyclohexyl

DIPEA:

Diisopropylethyl amine

DCE:

1,2-Dichloroethane

DIPPF:

1,1′-Bis(diisopropylphosphino)ferrocene

DME:

Dimethoxyethane

DMAD:

Dimethylaceylene dicarboxylate

DMEDA:

Dimethylethylenediamine

DMF:

Dimethylformamide

DMSO:

Dimethyl sulfoixde

DPEphos:

Oxydi-2,1-phenylene)bis(diphenylphosphine)

dppBz:

1,2-Bis(diphenylphosphino)benzene

dppe:

1,2-Bis(diphenylphosphino)ethane

dppf:

1,1′-Bis(diphenylphosphino)ferrocene

R-DTBM-Segphos:

[(4R)-(4,4′-bi-1,3-benzodioxole)-5,5′-diyl]bis[bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine]

ee:

Enantiomeric excess

EtOH:

Ethanol

HMPA:

Hexamethylphosphoramide

Imes:

1,3-bis(2,4,6-trimethylphenyl)-2,3-dihydro-1H-imidazaol-2-ylidene

i-PrOH:

Isopropanol or 2-methylpropanol

Josiphos:

(R)-1-[(S P)-2-(Di-tert-butylphosphino)ferrocenyl]ethylbis(2-methylphenyl)phosphine

LiHMDS:

Lithium bis(trimethylsilyl)amide

m-:

Meta substitution

Me:

Methyl

MLn:

Transition metal complex

n-BuLi:

n-Butyllithium

t-BuONa:

Sodium tert butoxide

NHC:

N-Heterocyclic carbine

o-:

Ortho substitution

OAc:

Acetate

OMs:

Methanesulfonate

p-:

Para substitution

P2–Et:

1-Ethyl-2,2,4,4,4-pentakis(dimethylamino)-2Λ5-catenadi(phosphazene)

Pd2dba3 :

Tris(dibenzylideneacetone)dipalladium(0)

Ph:

Phenyl

PhCH3 :

Toluene

PhH:

Benzene

PhCl:

Chlorobenzene

RhCl(PPh3)3 :

Wilkinson’s catalyst

SPhos:

2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

t-Bu:

Tert-butyl

t-BuOH:

Tert-Butanol

t-BuOK:

Potassium tert butoxide

THF:

Tetrahydrofuran

TMEDA:

Tetramethylethylenediamine

Tp*:

hydrotris(3,5-dimethylpyrazolyl)-borate

Xantphos:

4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

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  1. Department of Chemistry, University of British Columbia, Vancouver, BC, V6T 1Z1, Canada

    Paul Bichler & Jennifer A. Love

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  2. Jennifer A. Love
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  1. Sackler Fac. Exact Sciences, School of Chemístry, Tel Aviv University, Tel Aviv, 69978, Israel

    Arkadi Vigalok

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Bichler, P., Love, J.A. (2010). Organometallic Approaches to Carbon–Sulfur Bond Formation. In: Vigalok, A. (eds) C-X Bond Formation. Topics in Organometallic Chemistry, vol 31. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-12073-2_3

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