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Ruthenium in Catalysis pp 237–287Cite as

Catalytic Transformations of Alkynes via Ruthenium Vinylidene and Allenylidene Intermediates

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Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 48))

Abstract

Vinylidenes are high-energy tautomers of terminal alkynes and they can be stabilized by coordination with transition metals. The resulting metal-vinylidene species have interesting chemical properties that make their reactivity different to that of the free and metal π-coordinated alkynes: the carbon α to the metal is electrophilic whereas the β carbon is nucleophilic. Ruthenium is one of the most commonly used transition metals to stabilize vinylidenes and the resulting species can undergo a range of useful transformations. The most remarkable transformations are the regioselective anti-Markovnikov addition of different nucleophiles to catalytic ruthenium vinylidenes and the participation of the π system of catalytic ruthenium vinylidenes in pericyclic reactions. Ruthenium vinylidenes have also been employed as precatalysts in ring closing metathesis (RCM) or ring opening metathesis polymerization (ROMP).

Allenylidenes could be considered as divalent radicals derived from allenes. In a similar way to vinylidenes, allenylidenes can be stabilized by coordination with transition metals and again ruthenium is one of the most widely used metals. Metal-allenylidene complexes can be easily obtained from terminal propargylic alcohols by dehydration of the initially formed metal-hydroxyvinylidenes, in which the reactivity of these metal complexes is based on the electrophilic nature of Cα and Cγ, while Cβ is nucleophilic. Catalytic processes based on nucleophilic additions and pericyclic reactions involving the π system of ruthenium allenylidenes afford interesting new structures with high selectivity and atom economy.

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Abbreviations

9-BBN:

9-Borabicyclo[3.3.1]nonane

Ac:

Acetyl

acac:

Acetylacetonate

AIBN:

2,2′-Azobisisobutyronitrile

anhyd:

Anhydrous

Ar:

Aryl

Bn:

Benzyl

Boc:

Tert-butoxycarbonyl

Bp:

Boiling point

Bpy:

2,2′-Bipyridyl

Bu:

Butyl

Bz:

Benzoyl

CAN:

Ceric ammonium nitrate

cat:

Catalyst

Cbz:

Benzyloxycarbonyl

CIP:

Cahn–Ingold–Prelog

cod:

Cyclooctadiene

concd:

Concentrated

cot:

Cyclooctatetraene

Cp:

Cyclopentadienyl

CSA:

Camphorsulfonic acid

d:

Day(s)

DABCO:

1,4-Diazabicyclo[2.2.2]octane

DBN:

1,5-Diazabicyclo[4.3.0]non-5-ene

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DCC:

N,N-dicyclohexylcarbodiimide

DDQ:

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

de:

Diastereomeric excess (discouraged, see dr)

DEAD:

Diethyl azodicarboxylate

DET:

Diethyl tartrate

DIBALH:

Diisobutylaluminum hydride

DIPT:

Diisopropyl tartrate

DMAP:

4-(Dimethylamino)pyridine

DMB:

3,4-Dimethoxybenzyl

DME:

1,2-Dimethoxyethane

DMF:

Dimethylformamide

DMPU:

1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

DMSO:

Dimethyl sulfoxide

dppe:

Bis(diphenylphosphino)ethane

dppm:

Bis(diphenylphosphino)methane

dr:

Diastereomeric ratio

EDTA:

Ethylenediaminetetraacetic acid

ee :

Enantiomeric excess

equiv:

Equivalent(s)

Et:

Ethyl

Fmoc:

9-Fluorenylmethoxycarbonyl

h:

Hour(s)

HMPA:

Hexamethylphosphoric triamide

i-Pr:

Isopropyl

KHMDS:

Potassium hexamethyldisilazide, potassium bis(trimethylsilyl)amide

L:

Liter(s)

LDA:

Lithium diisopropylamide

LHMDS:

Lithium hexamethyldisilazide, lithium bis(trimethylsilyl)amide

LTMP:

Lithium 2,2,6,6-tetramethylpiperidide

m-CPBA:

m-Chloroperoxybenzoic acid

Me:

Methyl

MEM:

(2-Methoxyethoxy)methyl

Mes:

Mesityl, 2,4,6-trimethylphenyl (not methanesulfonyl)

min:

Minute(s)

mol:

Mole(s)

MOM:

Methoxymethyl

Ms:

Methanesulfonyl (mesyl)

nbd:

Norbornadiene

NBS:

N-bromosuccinimide

NCS:

N-chlorosuccinimide

Nu:

Nucleophile

op:

Optical purity (discouraged, see ee)

PCC:

Pyridinium chlorochromate

PDC:

Pyridinium dichromate

Ph:

Phenyl

phth:

Phthalate

PMB:

4-Methoxyphenyl

PNB:

4-Nitrobenzyl

PPA:

Poly(phosphoric acid)

PPTS:

Pyridinium p-toluenesulfonate

Pr:

Propyl

Pv:

Pivaloyl

py:

Pyridine

rt:

Room temperature

s:

Second(s)

s-Bu:

Sec-butyl

SEM:

2-(Trimethylsilyl)ethoxymethyl

TBAF:

Tetrabutylammonium fluoride

TBDMS:

Tert-butyldimethylsilyl

TBDPS:

Tert-butyldiphenylsilyl

t-Bu:

Tert-butyl

TCNE:

Tetracyanoethylene

Tf:

Trifluoromethanesulfonyl (triflyl)

TFA:

Trifluoroacetic acid

TFAA:

Trifluoroacetic anhydride

thexyl:

1,1,2-Trimethylpropyl

THF:

Tetrahydrofuran

THP:

Tetrahydropyran-2-yl

TIPDS:

1,1,3,3-Tetraisopropyldisiloxane-1,3-diyl

TIPS:

Triisopropylsilyl

TMEDA:

N,N,N',N'-tetramethyl-1,2-ethylenediamine

TMS:

Trimethylsilyl

Tol:

4-Methylphenyl

Tr:

Triphenylmethyl (trityl)

Ts:

Tosyl, 4-toluenesulfonyl

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Authors and Affiliations

  1. Departamento de Química Orgánica y Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS), Universidad de Santiago de Compostela, 15782, Santiago de Compostela, Spain

    Jesús A. Varela, Carlos González-Rodríguez & Carlos Saá

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  1. Jesús A. Varela
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  2. Carlos González-Rodríguez
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  3. Carlos Saá
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Correspondence to Carlos Saá .

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Editors and Affiliations

  1. Inst. des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université Rennes1, Rennes, France

    Pierre H. Dixneuf

  2. Inst. des Sciences Chimiques de Rennes, UMR 6226-CNRS-Université de Rennes1, Rennes, France

    Christian Bruneau

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Varela, J.A., González-Rodríguez, C., Saá, C. (2014). Catalytic Transformations of Alkynes via Ruthenium Vinylidene and Allenylidene Intermediates. In: Dixneuf, P., Bruneau, C. (eds) Ruthenium in Catalysis. Topics in Organometallic Chemistry, vol 48. Springer, Cham. https://doi.org/10.1007/3418_2014_81

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