Here’s a fairly nasty question from the cumulative exam I gave earlier this month. It really got the graduate students confused, but that’s ok – it is indeed a bizarre reaction. I learned about it several years ago, when I visited Professor Chiba’s lab in Japan. What you see is a process that amounts to radical cation-driven metathesis reaction. This is a good example of a process that goes by an unusual mechanism and accomplishes something that is well familiar to many. There is no need to compare the scope of this process to what we are accustomed to seeing in ruthenium catalyzed chemistry. This is not the point. We should still be thrilled when we get to see nifty tricks emerge in less conventional areas that are relatively underpopulated (I refer to electrosynthesis). This is the quintessential “outside the box” sort of stuff!

http://onlinelibrary.wiley.com/doi/10.1002/anie.200503656/abstract