Playing with radicals

Aromatic C–H amination has received a lot of attention over the last few years, and our efforts began late 2012. The goal was simple: create a nitrogen-centered radical and trap it with a heterocycle.

Oxidative Explorations of Taxanes

Our paper is now out. This ongoing project, although some might label as simple, requires many different types of oxidations, and all of which require many experiments to discover. You can read the paper and ask me questions or send me comments to your heart’s content, but in this post I will talk about the discovery process and tell some of the stories.

Open Flask Blog Turns 1

On a fateful day last February, Y. Brando, Dane, Will, and Hans were busy sitting around rumor-mongering upon the latest internet gossip (likely started by Hans in the first place). Dane was dwelling over his lack of Reddit karma when they were all interrupted by Mr. Phil Barden. Surprising all parties involved, as usual, P.S.B. suggested "if you can't beat them, join them." And thus, we invented Openflask. Our first post was on 2/26/2013. And in true fashion of a graduate student, we forgot its birthday.

Magic Methyl Effect

Character picture taken from “Wreck It Ralph”

      

      This week, the newest paper in our sulfinate chemistry series was published online, featuring a radical-based C–H methylation of heterocycles. Indeed, as we embarked on “mission methylation,” we were mesmerized by the “magic methyl effect” where appending a single methyl group in the appropriate place could improve the biological activities of pharmaceuticals as much as 100-fold. (See the elegant review by Tim Cernak: Angew.Chem. Int. Ed. 2013, 52, 12256; there are also two interesting blog entries “In the Pipeline” about the Magic Methyl Group in 2011 and 2013.

Believe Everything You Read on the Internet

Sometimes, rumors pop up on the internet. You should always believe them. Seriously. Nobody on the internet lies. Just the other day, I read that Phil Baran is not actually from New Jersey, but he is in fact part of an advanced alien invasion from Mars. Seriously. I read it on the internet. It must be true.

Structural Reassignment by Cool Science

Today, Vinogradova, Muller, and Buchwald have an excellent piece of investigative science in Angew. Chem. Int. Ed. that I think is great, just great. And honestly, I'm a bit jaded and easily unimpressed (especially when the work isn't directly applicable to me finishing my Ph.D.). In fact, I liked this paper enough to write about it, and not just tweet it on the sidebar <---over there.

Lets start with a summary of why I think its great.

1. They decided to take a closer look at a "known" system - and they learned something new.

2. They crystallized a liquid using the work by Fujita et al.

...And onward with a more in depth look...

Experiments with Googling

[Disclaimer - I couldn't think of any good images for this blog post, so to liven it up a bit here are a few things you can use: 1) An ASCII game you can play in your browser that is quite fun - pro tip - let it run in the background while you're at work, 2) The even better sequel, 3) A link to this post with Nyan Cat on top. And now on with the science.]

Searching the chemical literature is part of the process of doing bench chemistry, or even thinking about doing bench chemistry. I can't even fathom how much slower my days would be if I needed to go to the library to find a reaction instead of turning to "The Googlefox." These days, we've got all  kinds of methods for scouring the chemical literature, Scifinder and Reaxys being two of the best. Of course, there are other useful databases: the ACS has a search feature , SDBS is super useful, and you can even get a good deal of information from Sigma-Aldrich. I'm certain there are plenty more.

And yet... I turn to Google.