Monday, February 4, 2008

A new precatalyst for Heck Reactions

It's a beauty, isn't it? I mean, look at that monster! And it packs 4 palladium atoms per catalyst too. It just appeared in Organometallics (DOI: 10.1021/om7005613). They actually coupled together iodobenzene and styrene. The cool thing about this is that they could tune the reactivity of the catalyst by changing the metal complexed in the middle of the porphyrin. With M=MnCl it took almost 400 minutes for the reaction to complete, but with M=Mg it only took about 200 minutes. Ok, seriously. I don't mean to pick on Bart M. J. M. Suijkerbuijk, Sara D. Herreras Martínez, Gerard van Koten, and Robertus J. M. Klein Gebbink, but I really don't understand what the purpose of this research is. I guess you can get some understanding about the electronic nature of pincer ligands, but no one in their right mind would ever use something like this for a Heck reaction. It is pretty though. It even weighs 10 times more than your substrate. I guess that makes for easy weighing. Let's say you use 10 mol% of the catalyst. You can just use the same mass as iodobenzene and you're good to go.

2 comments:

Chemgeek said...

That looks like a freaky lolnano dude.

BSW said...

The point is you can use it in a continuous flow reactor, because it can be filtered out on a membrane. No, it's not useful for a benchtop chemist, but if you can get the continuous flow setup working (that is, the leech through the membrane sufficiently low), then you add one pinch...and never have to add any again, and you just keep using the reactor to make styrenes for days on your initial 1g of catalyst. Now, I don't think they're close to running that reactor, but I'm almost positive that's why they're making that dendrimeric structure.