Organozinc_compound.ppt

Organozinc compound
Organozinc compounds in organic chemistry contain carbon to zinc chemical bonds. Organozinc chemistry is the science of organozinc compounds describin
their physical properties, synthesis and re[1a][c2t]i[o3]n[4s].
Organozinc compounds were among the first organometallic compounds made. They are less reactive than many other analogous organometallic reagents,
such as Grignard and organolithium reagents. In 1848 Edward Frankland prepared the firs t orgOargnaonzoiznincc chemistry compound, diethylzinc, by heating
ethyl iodide in the presence of zinc[5m] eTthali.s reaction produced a volatile colorless liquid that
spontaneous combusted upon contact with air. Due to their pyrophoric nature, organozinc compounds are generally prepared u sing air-
free techniques. They are unstable toward protic solvents. For many purposes they are prepared in situ, not isolated, but many have been isolated as pure
saunbdstthaonrcoeusghly characterize[6d].
Organozincs can be categorized according to the number of carbon substituents that are bound to[2]t[h3]e metal.
1. Diorganozinc (R2Zn): A class of organozinc compounds in which two alkyl ligands. These may be further divided into subclasses depending on the other
ligands attached
2. Heteroleptic (RZnX): Compounds which an electronegative or monoanionic ligand (X), such as a halide, is attached to the zinc center with another alkyl or
aryl substituent (R).
3. Ionic organozinc compounds: This class is divided into organozincates (R nZn−) and organozinc cations (RZnLn
+).
Contents
Bonding Synthesis
From zinc metal
Functional group exchange
β-Silyl diorganozinc compounds Transmetallation
Reactions
Reformatsky reaction
Simmons–Smith reaction Titanium–zinc methylenation Negishi coupling
Fukuyama coupling Barbier reaction Zinc acetylides
Organozincates Synthesis Reactions
Organozinc(I) compounds See also
References External links
Bonding
In its coordination complexes zinc(II) adopts several coordination geometries, commonly octahedral, tetrahedral, and various pentacoordinate geometries.
structural flexibility can be attributed to zinc's electronic configuration [A10r]43sd2. The 3d orbital is filled, and therefore, ligand field effects are nonexistent.
Coordination geometry is thus determined largely by electrostatic and steric intera[2c] tOiorngsa.nozinc compounds usually are two- or three-coordinate,
reflecting the strongly donating property of the carbanionic ligands.
Typical diorganozinc complexes have the formu2lZanR. Dialkylzinc compounds are monomeric with a linear coordination at the zinc[7a] tAomp.olar covalent
bond
exists between carbon and zinc, being polarized toward carbon due to the differences in electronegativity values (carbon: 2.5 & zinc: 1.65). The dipole mom
symmetric diorganozinc reagents can be seen as zero in these linear complexes, which explains their solubility in nonpola r solvents like cyclohexane. Unlike
binary metal alkyls, the diorganozinc species show a low affinity for complexation with ethereal solvent. Bond2Zinng isindRescribed as employing sp-
hybridized orbitals on Zn[.2]
These structures cause zinc to have two bonding d-orbitals and three low-lying non-bonding d-orbitals (see non-bonding orbital), which are available for bin
When zinc lacks electron donating ligands it is unable to obtain coordination saturation, which is a consequence of the large atomic radius and low electron
defic of zinc. Therefore, it is rare for bridging alkyl or aryl groups to occur due to the weak electron deficiency of the zinc ato m. Although, it does occur in
some cases as Ph2Zn (Shown below) and which halogens are the organozinc can form metal clusters (see cluster chemistry). When a halogen li gand is
added to the zinc
both the acceptor and donor character of zinc is enhanced allowing for aggr[e2g] ation.

(2
Functional group exchange
The two most common zinc functional group interconversion reactions are with halides and boron, which is catalyzed by c opper iodide (CuI) or base. Th
b intermediate is synthesized by an initial hydroboration reaction followed by treatment with diethyl zinc. This synthesis shows the utility of organozin
reagent displaying high selectivity for the most reactive site in the molecule, as well as creating useful coupling[1p2a]rtners.
(2.5
This group transfer reaction can be used in allylation, or other coupling reactions (such as Negishi [c1o3]upling).
(2.4)
From zinc metal
Frankland's original synthesis of diethylzinc involves the reaction of ethyl iodide with zinc metal. The zinc must be activ ated to facilitate this redox reaction. O
such activated form of zinc employed by Frankland is zinc-copper c[o5]uple.
2 EtI + 2 Zn0 → Et 2Zn + ZnI2 (2.2)
Riecke zinc, produced by in situ reduction of Z2nwCilth potassium, is another activated form of zinc. This form has proven useful for reactions such as Negish
coupling and Fukuyama coupling. Formation of organozinc reagents is facilitated for alkyl or aryl halides bearing electron -withdrawing substituents, e.g.,
nitriles esters[.10][11]
(2.1)
Saturated diorganozinc reagents with bridging aryl groups
Synthesis
Several methods exist for the generation of organozinc compounds. Commercially available diorga nozinc compounds are dimethylzinc, diethylzinc and
diphenyl These reagents are expensive and difficult to handle. In one[8s][t9u] dthye active organozinc compound is obtained from much cheaper
organobromine precursors:

In this method zinc is activated by 1,2-dibromoethane and trimethylsilyl chloride. A key ingredient is lithium chloride which quickly forms a soluble adduc
with the organozinc compound thus removing it from the metal surface.
Reactions
In many of their reactions organozincs appear as intermediates.
In the Frankland–Duppa reaction (1863) an oxalate ester (ROCOCOOR) reacts with an alkyl halide R'X, zinc and hydrochloric acid to the α-
hydroxycarboxylic esters RR'COHCOOR[19]
Reformatsky reaction
This organic reaction can be employed to convert α-haloester and ketone or aldehyde to a β-hydroxyester. Acid is needed to protonate the resulting alkoxide
work up. The initial step is an oxidative addition of zinc metal into the carbon -halogen bond, thus forming a carbon-zinc enolate. This C-Zn enolate can
rearrange to the Oxygen-Zinc enolate via coordination. Once this is formed the other carbonyl containing starting material will coordinate in the manner shown
b and give the product after protonati[o20n]. The benefits of the Reformatsky reaction over the conventional aldol reaction protocols is the following:
1. Allows for exceedingly derivatized ketone substrates
2. The ester enolate intermediate can be formed in the presence of enolizable moieties
3. Well suited for intramolecular reactions
Below shows the six-membered transition state of the Zimmerman–Traxler model (Chelation Control, see Aldol reaction),3inis wsmhicahlleRr than R4.[21]
(2.10)
Organozinc can be obtained directly from zinc
m[e17ta][l1:8]
Transmetallation
Transmetallation is similar to the interconversions displayed above zinc can exchange with other metals such as mercury, lithium, copper, etc. One example
reaction is the reaction of diphenylmercury with zinc metal to form diphenylzinc and metallic mercury:
HgPh2 + Zn → ZnPh 2 + Hg (2.8)
The benefit of transmetalling to zinc it is often more tolerant of other functional groups in the molecule due to the low rea ctivity which increase[s15s]electivity.
In the synthesis of Maoecrystal V, a directed ortho metalation gives the initial aryl-lithium species, which is transmetallated to the desired arylzinc
compound. The arylzinc compound is significantly less reactive than the aryl-lithium species and thus better tolerates the functionality in the subsequent
coupling with methyl chlorooxaloacetate. Esters are significantly stable against organozinc reagents.[16]
(2.7)
β-Silyl diorganozinc compounds
One of the major drawbacks of diorganozinc alkylations is that only one of the two alkyl substituents is transferred. This pr oblem can be
solved3SbyiCuHs2in- g Me (TMSM), which is a non-transferable gro[u1p4].

Titanium–zinc methylenation
Organozinc compounds derived from methylene bromide or iodide can electrophilically add to carbonyl groups to form termin[2a4l] aTlhke nresa.ction is
mechanistically related to the Tebbe reaction and can be catalyzed by various Lewis acids4(eo.rgA. lT2iMCel 6).[25] The reaction is used to introduce deuteriu
into molecules for isotopic labeling or as an alternative to the Wittig reaction.
Negishi coupling
This powerful carbon-carbon bond forming cross-coupling reactions combines an organic halide and an organozinc halide reagent in the presence of a n
palladium catalyst. The organic halide reactant can be alkenyl, aryl, allyl, or propargyl. Alkylzinc coupling with alkyl halides such as bromides and chlorides
also been reported with active catalysts such as Pd-PEPPSI precatalysts, which strongly resist beta-hydride elimination (a common occurrence wi
substituents[)2. 6] Either diorganic species or organozinc halides can be used as coupling partners during the transmetallation step in th is reaction. Despite
reactivity of organozinc reagents on organic electrophiles, these reagents are among the most powerful metal nucleophiles towa[r2d7]palladium.
Alkylzinc species require the presence of at least a stoichiometric amount of halide ions in solution to form a "zincate" species of the3
2f−o,rbmefRorZenXit can
undergo transmetalation to the palladium ce[n28tr]e.This behavior contrasts greatly with the case of aryl zinc species. A key step in the catalytic cycle is
transmetalation in which a zinc halide exchanges its organic substituent for another ha logen with the metal center.
An elegant example of Negishi coupling is Furstner's synthesis of amphidinol[i2d9e] T1:
(3.6)
Although the mechanism has not been fully elaborated it is hypothesized that the organozinc intermediate is a metal -carbenoid. The intermediate is
believed t three-centered "butterfly-type". This intermediate can be directed by substituents, such as alcohols, to deliver the cyclopropane on the same side o
t he molecul copper couple is commonly used to activate [z2i1n]c.
(3.5)
Simmons–Smith reaction
The Simmons–Smith reagent is used to prepare cyclopropanes from olefin using methylene iodide as the methylene source. The reaction i s effected with
zin key zinc-intermediate formed is a carbenoid (iodomethyl)zinc iodide which reacts with alkenes to afford the cyclopropanated product. The rate of
forming the a zinc species is increased via ultrasonication since the initial reaction occurs at the surface of the metal.
(3.4)
The Reformatsky reaction even allows for with zinc homo-eno[2la3t]eAs.modification of the Reformatsky reaction is the Blaise
reac[t2i1o]n.
The Reformatsky reaction has been employed in numerous total syntheses such as the synthesis of C(16),C(18) -bis-epi-
c[y2t2o]chalasin D:

(3
(3.12
In the absence of ligands, the reaction is slow and inefficient. In the presence of chiral ligands, the reaction is fast and gives high conversion. Noyori
determined monozinc-ligand complex is the active spec[3ie5s] .
.
Zinc acetylides
The formation of the zinc acetylide proceeds via the intermediacy of a dialkynyl zinc (functional group exchange). Catalyti c processes have been developed
s Merck’s ephedrine proces[3s3.] Propargylic alcohols can be synthesized from zinc acetylides. These versatile intermediates can then be used for a wi de
rang chemical transformations such as cross-coupling reactions, hydrogenation, and pericyclic r[e34a]ctions.
Barbier reaction
The Barbier reaction involves nucleophilic addition of a carbanion equivalent to a carbonyl. The conversion is simila r to the Grignard reaction. Th
organo reagent is generated via an oxidative addition into the alkyl halide. The reaction produces a primary, secondary, or te rtiary alcohol via a 1,2
addition. The B reaction is advantageous because it is a one-pot process: the organozinc reagent is generated in the presence of the carbonyl substrate
Organozinc reagent alelsos water sensitive, thus this reaction can be conducted in water. Similar to the Grignard reaction, a Schlenk e quilibrium
applies, in which the more re dialkylzinc can be forme[d2.1]
(3.10
The mechanism resembles the Grignard reaction, in which the metal alkoxide can be generated by a radical stepwise pathw ay, through single electro
tran concerted reaction pathway via a cyclic transition state. An example of this reaction is in Danishefsky’s synthesis of c ycloproparadicicol. By using th
organ addition reaction conditions the other functionality of the dienone and the alkyne are to[l3e2r]ated:
Fukuyama coupling
Fukuyama coupling is a palladium-catalyzed reaction involving the coupling of an aryl, alkyl, allyl, or α,β- unsaturated thioester compound. This thioester
compo can be coupled to a wide range of organozinc reagents in order to reveal the correspond ing ketone product. This protocol is useful due to its
sensitivity to func groups such as ketone, acetate, aromatic halides, and even aldehydes. The chemoselectivity observed indicates ketone formatio n is more
facile than oxidative aodf pdaitilolandium into these other moieti[e30s].
(3.8
A further example of this coupling method is the synthesis of (+)-biotin. In this case, the Fukuyama coupling takes place with the t[3h1io] lactone:

Organozinc(I) compounds
Low valent organozinc compounds having a Zn–Zn bond are also known. The first such compound, decamethyldizincocene, was rep[4o0r]ted in
2004.
See also
(4.4)
Triorganozincates compounds are formed by treating a diorganozinc such3aSsiC(HM2e)2Zn with an alkali metal (K), or an alkali earth metal (Ba, Sr, or Ca).
One example is [(Me3SiCH2)3Zn]K. Triethylzincate degrades to sodium hydridoethylzincate(II) as a result of beta -hydride elim[3in9a] tion:
2 NaZnEt3 → Na 2Zn2H2Et4 + 2 C2H4 (4.3)
The product is an edge-shared bitetrahedral structure, with bridging hydride ligands.
Reactions
Although less commonly studied, organozincates often have increased reactivity and selectivity compared to the neutral diorganozinc compounds. They hav
useful in stereoselective alkylations of ketones and related carbonyls, ring opening reactions. Aryltrimethylzincates pa rticipate in vanadium mediated C-C for
reactions[.3]
Organozincates
The first organozinc ate complex (organozincate) was reported in 1858 by James Alfred W[38a]naknlyna,ssistant to Frankland and concerned the reaction of
elemental sodium with diethylzinc:
2 Na + 3 ZnEt2 → 2 NaZnEt 3 + Zn (4.1)
Organozinc compounds that are strongly Lewis acidic are vulnerable to nucleophilic attack b y alkali metals, such as sodium, and thus form these ‘ate compo
Two types of organozincates are recognized: tetraorganozinca4teZsn]M([R2), which are dianionic, and triorganozincates3Z([nR]M), which are monoanionic.
Their structures, which are determined by the ligands, have been extensively chara[3c]terized.
Synthesis
Tetraorganozincates such as [M4Zen]Li 2 can be formed by mixing M2eZn and MeLi in a 1:2 molar ratio of the rectants. Another example synthetic route to
forming spriocyclic organozincates is shown bel[o3w] :
(3.15)
The α-stereocenter of the ligand dictates observed stereochemistry of the propargylic alcohols
The steric effects between the aldehyde substituent and the ligand are less important but still dictate the favored conformat
ion
Zinc-acetylides are used in the HIV-1 reverse transcriptase inhibitor Efavirenz as well as in Merck’s ephedrine de[3r7iv]atives .
(3
Diastereoselectivity for addition of organozinc reagents into aldehydes can be predicted by the following model by Noyori and Dav[id36A] .
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Compounds of zinc
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External links
Zinc in organic synthesis (http://www.chem.wisc.edu/areas/reich/orgmet/zinc.htm) Organozinc Compounds produced by BASF Corporation
(http://www.rznx.basf.com)
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