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Topic: Decarboxylative Coupling  (Read 1496 times)

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Offline zsinger7

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Decarboxylative Coupling
« on: April 08, 2018, 11:00:27 AM »
All,
I am preparing to attempt an iteration of a synthesis using this coupling method, one I have never done before in the lab.  I have much experience with coupling reactions (Suzuki and Heck), but wanted input/advice on one thing.

One thing that literature rarely references (I have access to ACS pubs) is the applicability of this FGI regarding a couple with a carboxylic acid (obviously) and an METHYL-halide rather than an aryl halide.  Most literature examples use aryl halide. 

So:  Possible to use, say, methyl iodide to effectively decarboxylate with no consequent carbon loss (carbon is lost to CO2, but gained via the methyl iodide)?  Any experiences with this type of FGI? 

       Thanks!

Offline phth

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Re: Decarboxylative Coupling
« Reply #1 on: April 14, 2018, 12:51:09 AM »
Aryl iodides versus methyl iodides have significantly different reactivities. It may work, but I would not be surprised if it was slow i.e. side reactions outcompete the desired reaction. I'm not an expert in decarboxylative cross coupling. Are you familiar with the barton decarboxylation? Maybe you could trap the radical with a silane (hiyama coupling) or iodomethane (SET).

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