nice simple method

Saw this today in the JOC ASAPs.


I'm a fan of any new method, or method improvement that is simple, efficient, straightforward, and useful. While I haven't ever made a sulfonamide that wasn't a protecting group, they are handy for other things, and pop up in drugs as well. These guys got the reaction to work with one set of conditions on electron rich and poor aromatic thiols, a few aliphatic as well, and it appears to be selective and mild as well.

In fact the only things I can negatively comment on at all are that I would have liked to see more aliphatic examples, and acetonitrile is an expensive solvent. However, I bet that within the next year or so people will be buying cars in stupid numbers again, and acetonitrile will come back down in price.

Edit: I somehow gave the wrong journal title, but the right link. Thanks to Dr. Miller for pointing it out.

great idea

Yesterday our lab and another had the privilege to go have lunch with Philip S. Portoghese and see him give a seminar later. During lunch we were talking about journals and the state of the business of journals, he's been the editor of J. Med. Chem. for 37 years, and ACS's new headache inducing paper journal format where they have two pages of material per page of paper came up. I mentioned that it felt like I was reading a girlie magazine whenever I turned it sideways to flip through the issue, and someone else in attendance remarked that we should have a centerfold with a reaction or compound of the month. What an awesome idea! People would be vying for the cover with pretty pictures, but others would be competing to get the centerfold with great science! Truly an idea who's time has come!

edit:
I said something stupid, and would like to clarify. You usually get the cover by publishing good work, but the cover itself is something pretty that is related to the work, and usually not the work itself.

The centerfold could be pure, unadulterated, awesome science.

Somebody Explain

Am I missing something?



This is a really expensive and complicated way to do a sophomore organic reaction. Instead of making the silyl enol ether and treating it with stoichiometric CAN and 2,6-di-tBuPy (both expensive and used in large excess 2 eq and 4 eq respectively), why not just deprotonate with LDA and add an allyl halide?

Can anyone think of a reason to do this reaction (aside from somehow publishing it in Org Lett)?