jo0c00448_si_001.pdf (4.31 MB)
Synthesis of α‑Trifluoromethylthio-α,β-Unsaturated Carbonyl Compounds by DABCO-Mediated Electrophilic Trifluoromethylthiolation with N‑SCF3‑Dibenzenesulfonimide
journal contribution
posted on 2020-05-22, 15:06 authored by Jeyeon Yoo, Heun-Jong Ha, Bora Kim, Chang-Woo ChoA DABCO-mediated electrophilic α-trifluoromethylthiolation
of α,β-unsaturated carbonyl compounds comprising no β-substituents
has been achieved using N-trifluoromethylthio-dibenzenesulfonimide
as the SCF3 source. The direct trifluoromethylthiolation
provides the corresponding α-trifluoromethylthio-α,β-unsaturated
carbonyl products in good yields (up to 88%). Furthermore, the vinyl
group in the α-trifluoromethylthio-α,β-unsaturated
carbonyl product was successfully transformed into diverse functional
groups in good to excellent yields (70–95%) by reactions such
as epoxidation, aziridination, hydrocyanation, and hydrogenation.