Redox-Neutral Radical Cascade Cyclization of -Arylacrylamides with Unactivated Alkyl and Aryl Chlorides.

Herein, we report the first metal-free, redox-neutral strategy for radical cascade alkylative radical addition, cyclization of -arylacrylamides with unactivated alkyl chlorides to give corresponding 3,3-disubstituted oxindoles in moderate to good yields. This transformation's salient features are the utilization of an organo photocatalyst, mild reaction conditions, and broad substrate scope. Moreover, this methodology is suitable for hetero cycle derived acrylamides and further allowed to utilize aryl chlorides for radical cyclization reaction.

Photocatalytic Hydro Tri/Difluoromethylation of Alkenes with Bench Stable Tri/Difluoromethylating Reagents.

Herein, we demonstrate the synthesis and characterization of bench stable tri/difluoromethylating reagents and their potential applications in redox neutral hydro tri/difluoromethylation of alkenes enabled by visible light. The new tri/difluoromethylating reagents are obtained on a gram-scale through simply cyclocondensation of commercially available anthranilamide with phenyltrifluoro or difluoromethyl ketone. Preliminary mechanistic studies indicated that a canonical photoredox catalytic cycle is being operative.

Photoinduced Decarboxylative C3-H Alkylation of Quinoxalin-2(1)-ones.

An efficient, catalyst- and additive-free, visible-light-driven radical C3-H alkylation of quinoxalin-2(1)-one derivatives has been developed. This reaction utilizes alkyl-NHP-esters as an alkyl radical donor and quinoxalin-2(1)-one derivatives as an alkyl radical acceptor. The operationally simple protocol works under mild reaction conditions and tolerates a variety of functional groups.

Cerium photocatalyzed radical smiles rearrangement of 2-aryloxybenzoic acids.

We report herein a cerium photocatalyzed aryl migration from an aryl ether to a carboxylic acid group through radical-Smiles rearrangement. This operationally simple protocol utilizes inexpensive CeCl as a photocatalyst and converted a variety of 2-aryloxybenzoic acids into aryl-2-hydroxybenzoates in good yields.

Visible-Light Enabled C(s)-C(s) Cross-Electrophile Coupling via Synergistic Halogen-Atom Transfer (XAT) and Nickel Catalysis.

We herein report the first visible-light-mediated cross-coupling of unactivated alkyl iodides with aryl bromides through synergistic halogen atom transfer (XAT) and nickel catalysis. This simple protocol operates under mild reaction conditions and tolerates a variety of functional groups affording C(s)-C(s) cross-coupling products in good to moderate yields.

Cerium-photocatalyzed aerobic oxidation of benzylic alcohols to aldehydes and ketones.

We have developed a cerium-photocatalyzed aerobic oxidation of primary and secondary benzylic alcohols to aldehydes and ketones using inexpensive CeCl·7HO as photocatalyst and air oxygen as the terminal oxidant.