Generation of electrophilic phenyltellurium and phenylselenium species via photochemical electron transfer

Mechanistic and Synthetic Investigations on the Dual Selenium-π-Acid/Photoredox Catalysis in the Context of the Aerobic Dehydrogenative Lactonization of Alkenoic Acids

“…Thus, the design of new abiotic oxidase catalysis regimes that efficiently operate under a gas atmosphere with reduced oxygen concentrations (≤21 vol %) are highly sought after . Recently, we have disclosed the first selenium-π-acid/photoredox catalysis protocol that operates with air as a terminal and gratuitous oxidant. , This procedure was realized by the cooperative interplay of a diselane and a photoredox catalyst and allowed for the oxidative coupling of alkenes with a broad variety of carboxylic acids under aerial conditions. Cognate selenium-π-acid catalysis methods have so far exclusively involved the use of customary oxidants, such as iodine­(III) reagents, N -haloimides, and N -fluorobenzenesulfonimide (NFSI) .…”

Synthesis of Phenylselenopyrans and Lactones from Allylic Alcohols and Acids via Baylis‐Hillman Reaction

“…Inspired with the biological profile of pyran derivatives as well as organoselenium compounds, and in continuation of our efforts on the synthesis of potential biologically active scaffolds by utilizing Baylis‐Hillman chemistry, herein, we report the use of PhSeCl in the synthesis of cyclic ethers and lactones from unsaturated alcohols and acids derived from Baylis‐Hillman reaction. We introduced selenium based and practical method for the construction of O ‐heterocycles by cyclization of unsaturated hydroxy and unsaturated carboxylic acid compounds, a procedure accompanied by the introduction of the PhSe group into the organic framework and leading to the phenylselenopyrans and lactones, respectively.…”