Remote Allylation of Unactivated C(sp 3 )–H Bonds Triggered by Photogenerated Amidyl Radicals

Followed the procedure as written for substrate S28, but some notes roughly in order of importance:

1) The product is very volatile! I highly recommend using diethyl ether the entire time instead of ethyl acetate. I rinsed with ether after quenching and then ran the column in ether/pentane. I also rotavapped in a 0 ºC ice bath carefully only until the ether and pentane were gone (or mostly gone). This successfully reproduced their yield of ~ 70-75 %, whereas if I rotavapped at higher temperatures or used ethyl acetate / hexanes as they reported, I struggled to get more than maybe 20 % yield.

2) Add the propargyl alcohol (I recommend purifying beforehand, which I did via SiO2 column with ether / pentane) very slowly. It is very reactive and tends to pop / splatter the reaction mixture even when adding dropwise. Add down the side of the reaction vessel. Might not hurt to cool to 0 ºC during the addition as well.

3) I heated the reaction to 50 ºC in a pressure tube despite the solvent being ether instead of THF in the procedure the SI refers you to.

4) Quenching with the sodium sulfate decahydrate is pretty messy so just add it slowly and stir rapidly.

Otherwise works great!