Highly Regioselective Synthesis of N‐β‐trifluoromethyl 2‐pyridones via anti‐Markovnikov Hydroamination of α‐(trifluoromethyl)styrenes with 2‐pyridones

Abstract

A novel and facile method for the synthesis of N-β-CF 3 -substituted 2-pyridones via hydroamination of α-(trifluoromethyl)styrenes with 2-pyridones was described. The reaction proceeded smoothly at room temperature, affording a variety of N-(β-trifluoromethyl-β-arylethyl)pyridin-2(1H)ones in moderate to good yields with excellent N-regioselectivity.

Water-promoted defluorinative synthesis of fluoroalkylated 1,5-diazapentadienes by using (NH4)2CO3 as an NH2 and NH source

“…On the basis of the abovementioned experimental observations and previous literature, 14–22 two possible reaction mechanisms for the H 2 O-promoted and (NH 4 ) 2 CO 3 -enabled deiodoamination-defluoroiminization cascade of perfluoroalkyl alkenes is proposed in Scheme 3. Initially, perfluoroalkyl alkene 1 readily undergoes S N V-type C(sp 2 )–I bond displacement with a molecule of NH 3 to generate enamine B .…”

“…1C). 16,17 As a continuation of our research efforts in defluorination reactions, 18 herein we describe a H 2 O-promoted and (NH 4 ) 2 CO 3 -enabled defluorination of fluoroalkyl alkenes under transition-metal-free conditions (Fig. 1D).…”