Visible-light-induced radical cyclization of N-allylbenzamide with [Bis(difluoroacetoxy)iodo]benzene to difluoromethylated dihydroisoquinolinones

Recent Advances in Visible Light‐Mediated Radical Fluoro‐alkylation, ‐alkoxylation, ‐alkylthiolation, ‐alkylselenolation, and ‐alkylamination

“…These two protocols provide the compounds in great yields in the absence of exogenous oxidants, photocatalysts, or electrochemical setups, which have been previously used for the synthesis of difluoromethylated 2‐oxindoles. Similar additive‐free difluoromethylation protocols were reported by Lu and coworkers to provide difluoromethyl dihydroisoquinolinones, spiro[4.5]trienones, and coumarins all utilizing additive‐free conditions [63–65] . A reduction with a photocatalyst can also provide the decarboxylative radical generation, as shown by Zhu, Wu, and coworkers in their difluoromethylated dibenzazepine synthesis [66] .…”

“…Similar additive-free difluoromethylation protocols were reported by Lu and coworkers to provide difluoromethyl dihydroisoquinolinones, spiro [4.5]trienones, and coumarins all utilizing additive-free conditions. [63][64][65] A reduction with a photocatalyst can also provide the decarboxylative radical generation, as shown by Zhu, Wu, and coworkers in their difluoromethylated dibenzazepine synthesis. [66] He and coworkers reported the synthesis of difluoromethyl ring fused quinazolinones under violet light irradiation utilizing 16, which was generated in situ.…”

Visible Light Mediated Halogen Atom Transfer to Access Polyhalogenated and Deuterated Lactams from Alkyl Halides

“…In both cases, the temperature surrounding the reaction vial was measured to be 40-43 °C, thereby excluding a temperature effect. Various control experiments were performed which revealed that light, photocatalyst, tertiary amine, and oxidant were indispensable for a successful transformation (Table 1, entries [13][14][15][16]. We also determined that reducing the amount of the peroxide led to diminished yield of the product (Table 1, entry 17).…”

“…[11] The recent demonstration of photochemical approaches [12] for XAT has significantly improved the sustainability quotient of this strategy (Scheme 1b), and the ability to activate haloalkanes photochemically but independent of their redox potential has profound implications for the generation of halogenated organics. Our interest in the develop-ment of new strategies for haloalkylation led us to dihydroisoquinolinones, [13] which are constituents of the core skeleton of various natural products and biologically active molecules [14] (Figure 1). Methods towards non-halogenated congeners include two-component cyclizations of homophthalic anhydrides and imines [15] and via directed CÀ H activation.…”