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Hello, welcome to our fourth exercise of this week.

We start right away with the first task and the choice.

Your Hextil and Suzuki reaction, what is the difference and what is the disadvantage of each reaction?

The Hextil reaction is the coupling reaction between olefins and arylaloginins or vinylaloginins

and a palladium complex is used as a catalyst.

The Hextil reaction is also a palladium-catalyzed coupling, but between arylaloginins and arylaloginins.

These arylaloginins are simply organazine connections.

We also have the Suzuki coupling, the Suzuki reaction, which takes place between organoboilants and arylaloginins

and is also catalyzed by a palladium complex.

In summary, the three reactions are cross-cutting, that is, catalyzed carbon-carbon binding connections,

where the same metal palladium is used as a catalyst.

And to better compare them, you should also understand the whole mecanism.

For example, here we have the whole catalyst cycle of a Hextil coupling.

The first line is the oxidative addition of halogenin.

This means that two new palladium bonds are created by the addition of this connection

and the metal is now oxidized from zero to palladium two.

Now comes the olefin coordination and injection between the marilic situent and the metal.

This is also exactly here between this carbon-metal bond.

Then comes a beta-hydride elimination.

This beta-water atom is transferred as a group of cells to the metal atom.

And here is a carbon-carbon double bond between the olefin in blue and the aryl in black.

And my target product is eliminated afterwards.

And finally there is a reductive elimination.

Here hydrogen and brome are eliminated as brome hydrogen atoms.

And therefore the oxidation levels of palladium from two to zero are reduced.

And this is how the metal, the catalyst, is generated.

Now comes the Hextil coupling.

As starting point we have our active palladium complex.

First we have an oxidative addition of organohalogenin.

Then it is oxidized.

We then have a transmetallidation reaction with the organocene connection.

And what happens?

The very organic rest of the organocene connection is transferred to the palladium.

And thus it is removed from the allogium.

Finally, there is also a reductive elimination of my target product,

where the catalyst is reduced and regenerated.

And now the Suzuki coupling.

Here are my ducts, an aryl halogenin and an organoboilant.

It is the same at the beginning as with the other last reactions.

It starts here with the oxidative addition of aryl halogenin.

Then comes this whole transmetallidation,

where this aryl rest of the acid is transferred to the palladium.

And how does this happen?

A base is used, for example sodium hydroxide.

By the addition of sodium hydroxide, organopalladium hydroxide is created.

And the halogen is also removed.

This base will also react with the acid to form an organoboilant acid.

And this, this salt, reacts with the palladium hydroxide complex further,

whereby the hydroxide ion is replaced by this aryl group.

And finally, there is also a reductive elimination of the product

Teil eines Kapitels:
Übungsaufgabe 4

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Offener Zugang

Dauer

00:08:24 Min

Aufnahmedatum

2020-12-07

Hochgeladen am

2020-12-07 14:00:00

Sprache

de-DE

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