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A mild light-induced cleavage of the S–O bond of aryl sulfonate esters enables efficient sulfonylation of vinylarenes

https://doi.org/10.1039/C8SC02769B

Ratushnyy, Maxim; Kamenova, Monika; Gevorgyan, Vladimir (January 2018, Chemical Science)

A new mode of S–O bond activation has been discovered, which constitutes novel reactivity of easily available and bench-stable arylsulfonate phenol esters. This protocol enables access to putative sulfonyl radical intermediates, which enable straightforward access to valuable vinyl sulfones.
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Palladium‐Catalyzed Atom‐Transfer Radical Cyclization at Remote Unactivated C(sp ³ )−H Sites: Hydrogen‐Atom Transfer of Hybrid Vinyl Palladium Radical Intermediates

https://doi.org/10.1002/anie.201712775

Ratushnyy, Maxim; Parasram, Marvin; Wang, Yang; Gevorgyan, Vladimir (February 2018, Angewandte Chemie International Edition)

Abstract A novel mild, visible‐light‐induced palladium‐catalyzed hydrogen atom translocation/atom‐transfer radical cyclization (HAT/ATRC) cascade has been developed. This protocol involves a 1,5‐HAT process of previously unknown hybrid vinyl palladium radical intermediates, thus leading to iodomethyl carbo‐ and heterocyclic structures.
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Visible‐Light‐Induced Palladium‐Catalyzed Generation of Aryl Radicals from Aryl Triflates

https://doi.org/10.1002/ange.201915962

Ratushnyy, Maxim; Kvasovs, Nikita; Sarkar, Sumon; Gevorgyan, Vladimir (April 2020, Angewandte Chemie)

Abstract A mild visible‐light‐induced Pd‐catalyzed intramolecular C−H arylation of amides is reported. The method operates by cleavage of a C(sp²)−O bond, leading to hybrid aryl Pd‐radical intermediates. The following 1,5‐hydrogen atom translocation, intramolecular cyclization, and rearomatization steps lead to valuable oxindole and isoindoline‐1‐one motifs. Notably, this method provides access to products with readily enolizable functional groups that are incompatible with traditional Pd‐catalyzed conditions.
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