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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: cheesewithwhine on November 12, 2013, 09:13:30 PM

Title: Trying to figure out a Pd catalysis reaction.
Post by: cheesewithwhine on November 12, 2013, 09:13:30 PM

(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2F7JL7OaD.png%3F1&hash=d48d532fb5a63416efd4766022cc7d69670d8af7)

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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Title: Re: Trying to figure out a Pd catalysis reaction.
Post by: AlphaScent 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. 

Title: Re: Trying to figure out a Pd catalysis reaction.
Post by: AlphaScent on November 13, 2013, 11:31:19 AM

Also, I think you drew your diester wrong.  Oxygen will not have 4 bonds.

Title: Re: Trying to figure out a Pd catalysis reaction.
Post by: AlphaScent 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

Title: Re: Trying to figure out a Pd catalysis reaction.
Post by: mst 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..

Title: Re: Trying to figure out a Pd catalysis reaction.
Post by: clarkstill on November 13, 2013, 12:43:38 PM

I suggest you look at the Tsuji-Trost reaction...

Title: Re: Trying to figure out a Pd catalysis reaction.
Post by: AlphaScent on November 13, 2013, 01:46:14 PM

Great call.

Awesome chemistry.

I will definitely be reading about this.