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Topic: Trying to figure out a Pd catalysis reaction.  (Read 2534 times)

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Offline cheesewithwhine

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Trying to figure out a Pd catalysis reaction.
« on: November 12, 2013, 09:13:30 PM »


I'm trying to figure out the product of this reaction. For the life of me I can't figure out what the ester is for, it doesn't look like a nucleophile. Thanks!


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« Last Edit: November 13, 2013, 01:12:01 PM by Dan »

Offline AlphaScent

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Re: Trying to figure out a Pd catalysis reaction.
« Reply #1 on: November 13, 2013, 11:24:31 AM »
This is a type of palladium cross-coupling facilitated by tetrakis.  I am used to halides like in Heck reactions.  Where is this from?  Do you have any back round to it?  I am hesitant to say the allylic acetate is the best leaving group. 
If you're not part of the solution, then you're part of the precipitate

Offline AlphaScent

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Re: Trying to figure out a Pd catalysis reaction.
« Reply #2 on: November 13, 2013, 11:31:19 AM »
Also, I think you drew your diester wrong.  Oxygen will not have 4 bonds.
If you're not part of the solution, then you're part of the precipitate

Offline AlphaScent

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Re: Trying to figure out a Pd catalysis reaction.
« Reply #3 on: November 13, 2013, 11:35:01 AM »
Seems that the enol form of the malonate diester will complex with platinum.  If you have access to journals this may be a good paper for you to read.  I base this only off the abstract.

http://pubs.rsc.org/en/content/articlelanding/1970/C2/c29700000198#!divAbstract
If you're not part of the solution, then you're part of the precipitate

Offline mst

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Re: Trying to figure out a Pd catalysis reaction.
« Reply #4 on: November 13, 2013, 11:46:30 AM »
Misread sorry

Initially I thought they were aiming for deprotonation of the diester by NEt3 to create a nucleophile, but I think you need stronger bases for that..
« Last Edit: November 13, 2013, 12:06:50 PM by mst »

Offline clarkstill

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Re: Trying to figure out a Pd catalysis reaction.
« Reply #5 on: November 13, 2013, 12:43:38 PM »
I suggest you look at the Tsuji-Trost reaction...

Offline AlphaScent

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Re: Trying to figure out a Pd catalysis reaction.
« Reply #6 on: November 13, 2013, 01:46:14 PM »
Great call.

Awesome chemistry.

I will definitely be reading about this.
If you're not part of the solution, then you're part of the precipitate

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