ol9b01430_si_001.pdf (3.84 MB)
tert-Butyl Nitrite Mediated Synthesis of 1,2,4-Oxadiazol-5(4H)‑ones from Terminal Aryl Alkenes
journal contribution
posted on 2019-06-17, 00:00 authored by Prasenjit Sau, Amitava Rakshit, Tipu Alam, Hemant Kumar Srivastava, Bhisma K. Pateltert-Butyl nitrite (TBN) mediated synthesis of
3-aryl-1,2,4-oxadiazol-5(4H)-ones has been accomplished
using terminal aryl alkenes via a biradical reaction intermediate.
Three consecutive sp2 C–H bond functionalizations
of styrenes afforded 3-phenyl-1,2,4-oxadiazol-5(4H)-ones via the formation of new CN, CO, C–O,
and two C–N bonds. Both of the N atoms originate from TBN,
while the carbonyl oxygen is from the water (moisture) the other oxygen
from the NO part of the TBN.
