Catalytic Transformations of Alkynes via Ruthenium Vinylidene and Allenylidene Intermediates

  • Jesús A. Varela
  • Carlos González-Rodríguez
  • Carlos Saá
Chapter
First Online:
Part of the Topics in Organometallic Chemistry book series (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.

Keywords

Ruthenium allenylidenes Ruthenium catalysis Ruthenium vinylidenes 

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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Copyright information

© Springer-Verlag Berlin Heidelberg 2014

Authors and Affiliations

  • Jesús A. Varela
    • 1
  • Carlos González-Rodríguez
    • 1
  • Carlos Saá
    • 1
  1. 1.Departamento de Química Orgánica y Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS)Universidad de Santiago de CompostelaSantiago de CompostelaSpain

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