Dilauroyl Peroxide

Intermolecular Radical Mediated Anti-Markovnikov Alkene Hydroamination Using N-Hydroxyphthalimide

“…Benzoyl peroxide (entry 5), and di- tert -butylperoxide (entry 6) produced only small amounts of 1a , but dilauroyl peroxide (entry 7) resulted in nearly exclusive hydroamination of n -butyl vinyl ether (94:6 1a : 1b ) producing 1a in 79% yield at 90 °C in 20 min. To eliminate the undesired polar addition leading to 1b , which is likely increased at higher reaction temperatures, we tested tert -butyl hyponitrite, which fragments at much lower temperatures compared to AIBN, benzoyl peroxide, di- tert -butylperoxide, or dilauroyl peroxide. , Using tert -butyl hyponitrite at 35 °C resulted in clean conversion to 1a in 82% yield (entry 8). A control reaction showed that 1a is not formed in the absence of triethyl phosphite (entry 9).…”