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.