End of Semester Blog

We were asked to read and comment on a publication on Christina White's website. I chose Publication #19. It dealt with the synthesis of complex allylic esters via C-H oxidation vs C-C bond formation. Here is the picture of the reaction scheme and catalyst:

One of the most important reactions in organic synthesis is esterification. It involves coupling preoxidized carboxylic acid and alcohol fragments. Coupling usually involves stoichiometric amounts of a condensation reagent or the generation of an activated, most of the time unstable, acid derivative. Catalytic esterification methods do exist but they suffer from a limited scope, so they often require one coupling partner to be used in excess. A great advancement would be a catalytic general esterification method that oxidatively couples a hydrocarbon with a carboxylic acid.


This study introduced the first general, selective C-H oxidation method for the direct synthesis of complex allylic esters. Based on the generality and predictable selectivity of this C-H oxidation method along with the strategic advantages it enables, White and her team anticipate that it will find widespread use in complex

molecule syntheses

I enjoyed reading this publication. I found it relatively easy to understand because of everything I have learned in Organic Chemistry. There is a lot of information in the publication and many more reaction schemes to look at. I would recommend that each of you read this publication for yourselves. There is also an example of Grubb's reaction, which we just went over in class. White and her team did a great job writing this publication. It was very interesting!

Source:
http://www.scs.illinois.edu/white/pubs/pub19.pdf