Photoredox-neutral ring-opening pyridylation of cyclic oximes via phosphoranyl radical-mediated N O/C C bond cleavages and sequential radical-radical coupling

A theoretical study of selective radical relay and coupling reactions for alkene difunctionalization

“…The homolytic cleavage of certain relatively weak bonds, such as O-O or N-O bonds [24][25][26][27][28] for which the bond dissociation energy is less than 60 kcal mol −1 , by energy inputs such as light or heat could afford amino or alkoxy radicals. These radicals could subsequently interact with alkenes to generate various radical intermediates (Scheme 1b).…”

Additive-free aerobic oxidative difunctionalization of alkenes with P4S10 and alcohols to access β-hydroxy phosphorodithioates

“…In continuation of our research toward the construction of phosphorus- and sulfur-containing compounds, 14,15 herein, we wish to report a facile and efficient protocol for the synthesis of a series of β-hydroxy phosphorodithioates through additive-free aerobic oxidative difunctionalization of alkenes with P 4 S 10 and alcohols under mild conditions (Scheme 1e). Interestingly, when 2-vinylpyridine and α,β-unsaturated carbonyl compounds were used as substrates, the hydrophosphorodithiolation products could be selectively obtained in good yields.…”

Organophotocatalytic cascade cyclization reactions for the synthesis of cyanoalkyl indole[2,1-a]isoquinolinones

“…Recently, Wei's group introduced cyanoalkyl into benzimidazo/indolo[2,1- a ]isoquinolin-6(5 H )-ones by using CuCl as a catalyst and K 2 S 2 O 8 as an oxidant under heating conditions. 8 Visible-light-induced imine radical-mediated selective C–C bond cleavage of cyclobutanone oxime derivatives to form cyanoalkyl radicals has attracted considerable attention in recent years, 9 in which a series of cascade cyclization reactions have achieved some results. 10 For example, in 2018, Chen and Xiao et al reported photocatalytic radical addition/cyclization for the synthesis of 1,2,3,4-tetrahydrophenanthrene by using fac -Ir(ppy) 3 as a photocatalyst and LiCO 3 as a base.…”