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Trying to figure out a Pd catalysis reaction.
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Topic: Trying to figure out a Pd catalysis reaction. (Read 2534 times)
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cheesewithwhine
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Trying to figure out a Pd catalysis reaction.
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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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. Dan
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Last Edit: November 13, 2013, 01:12:01 PM by Dan
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AlphaScent
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Re: Trying to figure out a Pd catalysis reaction.
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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.
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AlphaScent
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Re: Trying to figure out a Pd catalysis reaction.
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Reply #2 on:
November 13, 2013, 11:31:19 AM »
Also, I think you drew your diester wrong. Oxygen will not have 4 bonds.
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AlphaScent
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Re: Trying to figure out a Pd catalysis reaction.
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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
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mst
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Re: Trying to figure out a Pd catalysis reaction.
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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..
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Last Edit: November 13, 2013, 12:06:50 PM by mst
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clarkstill
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Re: Trying to figure out a Pd catalysis reaction.
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Reply #5 on:
November 13, 2013, 12:43:38 PM »
I suggest you look at the Tsuji-Trost reaction...
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AlphaScent
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Re: Trying to figure out a Pd catalysis reaction.
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Reply #6 on:
November 13, 2013, 01:46:14 PM »
Great call.
Awesome chemistry.
I will definitely be reading about this.
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Trying to figure out a Pd catalysis reaction.