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We report a vinyl radical-mediated 1,5-hydrogen atom transfer (1,5-HAT) strategy for the remote C(sp 3 )-H functionalization reaction, which includes cyanation, oxidation, and etherification under visible-light-induced photochemical conditions. This reaction is achieved using readily available alkyl N -hydroxyphthalimide esters as radical precursors, which can efficiently react with diverse alkynes to form key vinyl radical intermediates followed by a 1,5-HAT process. A series of structurally diverse γ-cyano, γ-carbonyl, and γ-oxygenated alkenes with excellent stereoselectivity can be efficiently constructed by this synthetic protocol.

A novel visible-light-induced trifluoromethylarylation/1,4-aryl shift/desulfonylation cascade reaction using CF3SO2Cl as CF3 source was described. The protocol provides an efficient approach for the synthesis of α-aryl-β-trifluoromethyl amides and/or CF3-containing oxindoles as well as the isoquinolinediones under benign conditions.

Herein, we reported the electrochemical hydroboration of olefins to access the organoboron derivatives in a one‐pot reaction under air and at room temperature. This reaction manifold was applied to a broad range of alkenes with 40–90% yields and good functional group tolerance without using a metal catalyst or an additional hydride source. Mechanistic studies suggested that this anodic oxidation conducted in an undivided cell allowing the production of a boron radical species, which initiates the hydroboration of olefins event by a radical addition process. [ABSTRACT FROM AUTHOR]

Cyclic compounds constitute a great important class of substances in the science of medicine and biology, which renders the research on facile and efficient construction of such complex scaffolds from simple starting materials to be hot and appealing. Recently, the radical cascade reaction involving multiple bond formation/cleavage has emerged as an ideal and powerful route to give high‐value cyclic products, along with diminished cost and waste. As a simple and benign methodology, photoredox catalysis offers a readily available access to the generation of radical species. Alkenes have been recognized as one of the most valuable building blocks for the reason they allow installation of different functional groups simultaneously through addition to the C=C bonds. This account summarizes the recent advances in photoinduced radical cascade cyclization to the synthesis of cyclic compounds with C=C bonds working as the initial radical acceptors, and emphasis is put on the related reaction mechanisms. The radical cascade reaction has emerged as a powerful route to afford valuable cyclic products, which enabled multiple bond formation in one step with diminished cost and waste. As a simple and mild methodology, photoredox catalysis offers a readily available access to the generation of radical species. This account summarizes the recent advances in photoinduced radical cascade cyclization of C=C bonds to the synthesis of cyclic compounds. [ABSTRACT FROM AUTHOR]

A novel visible-light-induced intramolecular chloroetherfication of electron-enriched styrenes is described. This approach provides a mild, alternative access to the synthesis of chlorinated tetrahydrofurans and tetrahydropyrans with high regio- and stereoselectivity. [ABSTRACT FROM AUTHOR]

New chiral phosphorus-olefin hybrid ligands derived from the rigid 'privileged' l-proline have been conveniently prepared and applied in the rhodium-catalyzed asymmetric arylation of electron-deficient olefins with arylboronic acids at room temperature; this reaction provides the desired products in excellent yields and high enantioselectivities. The origin of observed stereoselectivity has been investigated by density functional theory (DFT) calculations. [ABSTRACT FROM AUTHOR]

A metal-free and cost-effective synthetic protocol for selective aryltrifluoromethylation of allylic alcohols with Langlois' reagent (CF3SO2Na) through cascade trifluoromethyl radical addition/1,2-aryl migration has been developed. The highlights of this procedure are operational simplicity, excellent functional group tolerance, and mild reaction conditions. [ABSTRACT FROM AUTHOR]

An environmentally benign and metal-free [3+2]-cycloaddition of phenols and styrenes with sodium persulfate as an oxidant affords dihydrobenzofurans. [ABSTRACT FROM AUTHOR]

α,β-Unsaturated imide alkenes are found to undergo a visible light induced trifluoromethylarylation/1,4-aryl shift/desulfonylation cascade to yield oxindoles. [ABSTRACT FROM AUTHOR]

The aroyl radical in situ generated from a photocleavage reaction, is added to acrylamide compounds followed by cyclization to give oxindoles. [ABSTRACT FROM AUTHOR]

Irradiation of ortho-formyl dienes with UV light leads to benzobicycloheptanones in high yields and chemoselectivities via a photogenerated ketene methide/Diels-Alder cascade reaction. [ABSTRACT FROM AUTHOR]