ArticleNature communications2022
Organophotoredox-catalyzed semipinacol rearrangement via radical-polar crossover.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 49 citations in OpenAlex.
- Article
- Organo-catalyzed photoelectrochemical ring-contraction of arylidenecyclobutanolsChemical science · 2026Article
- Photocatalytic Aminoarylation of Styrenes.Organic letters · 2026Article
- Oxidative Scission of Bicyclo[2.2.2]octenones: Untying the α-Dimethoxycarbonyl.The Journal of organic chemistry · 2025Article
- Enantioselective Synthesis of α-Aryl Ketones by a Cobalt-Catalyzed Semipinacol Rearrangement.Angewandte Chemie (International ed. in English) · 2025Article
- Synthesis of tertiary alkylphosphonate oligonucleotides through light-driven radical-polar crossover reactions.Nature communications · 2023Article
- Organophotocatalytic carbo-heterofunctionalization of unactivated olefins with pendant nucleophiles.Chemical science · 2023Article
- Intermolecular Organophotocatalytic Cyclopropanation of Unactivated Olefins.Journal of the American Chemical Society · 2023Article
- Radical Redox Annulations: A General Light-Driven Method for the Synthesis of Saturated Heterocycles.ACS catalysis · 2022Article
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Authors and funding
3 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Over the past century, significant progress in semipinacol rearrangement involving 1,2-migration of α-hydroxy carbocations has been made in the areas of catalysis and total synthesis of natural products. To access the α-hydroxy carbocation intermediate, conventional acid-mediated or electrochemical approaches have been employed. However, the photochemical semipinacol rearrangement has been underdeveloped. Herein, we report the organophotoredox-catalyzed semipinacol rearrangement via radical-polar crossover (RPC). A phenothiazine-based organophotoredox catalyst facilitates the generation of an α-hydroxy non-benzylic alkyl radical followed by oxidation to the corresponding carbocation, which can be exploited to undergo the semipinacol rearrangement. As a result, the photochemical approach enables decarboxylative semipinacol rearrangement of β-hydroxycarboxylic acid derivatives and alkylative semipinacol type rearrangement of allyl alcohols with carbon electrophiles, producing α-quaternary or α-tertiary carbonyls bearing sp
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