ArticleJournal of the American Chemical Society2023
Expanding Reaction Profile of Allyl Carboxylates via 1,2-Radical Migration (RaM): Visible-Light-Induced Phosphine-Catalyzed 1,3-Carbobromination of Allyl Carboxylates.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 63 citations in OpenAlex.
- 1,2-Migration of oxamoyl-protected alcohols via reversible C-H sampling.National science review · 2026Article
- N-O Dual Functional Group Transposition via Energy Transfer Photocatalysis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Photoinduced Selective Construction of Densely Functionalized Spirocyclic Ethers With Carbyne Equivalents.Angewandte Chemie (International ed. in English) · 2026Article
- Redox-mediated domino electrosynthesis of N,N-dimethylformamide with industrial-relevant productivity and modularized cathodic integration.Nature communications · 2026Article
- Article
- Halogen bonding-induced 1,3-carbohydroxylation of allyl carboxylatesChemical science · 2026Article
- Biomimetic sulfur-catalyzed carbonyl transfer enables the carbonylative difunctionalization of unactivated alkenes.Chemical science · 2026Article
- Article
- Highly stereoselective synthesis of polysubstituted housanes and spiro-oxa-housanes: application and mechanistic insights.Chemical science · 2025Article
- Catalytic 1,2-Radical Acyloxy Migration: A Strategy to Access Novel Chemical Space and Reaction Profiles.Accounts of chemical research · 2025Article
- Photocatalytic 1,3-difluoroalkylcarboxylation of alkenes by triple kinetic-controlled radical self-ordering.Chemical science · 2025Article
- A New Reaction Framework for Allyl Carboxylates.Trends in chemistry · 2025Article
- Copper-Catalyzed 1,4-Aminohydroxylation and Aminothiolation of 1,3-Dienes by Carbonyl-Assisted Migration.Chem catalysis · 2024Article
- Direct oxygen insertion into C-C bond of styrenes with air.Nature communications · 2024Article
- Regio- and stereoselective access to highly substituted vinylphosphine oxides via metal-free electrophilic phosphonoiodination of alkynes.Nature communications · 2024Article
- Photogeneration of α-Bimetalloid Radicals via Selective Activation of Multifunctional C1 Units.Journal of the American Chemical Society · 2024Article
- Mechanistic Studies on the 1,2-Spin-Center Shift in Carbohydrate Systems with a Fluorenylcyclopropyl Radical Clock.The Journal of organic chemistry · 2023Article
Corrections and comments
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
Abstract
Allyl carboxylates are useful synthetic intermediates in a variety of organic transformations, including catalytic nucleophilic/electrophilic allylic substitution reactions and 1,2-difunctionalization reactions. However, the catalytic 1,3-difunctionalization of allyl carboxylates remains elusive. Herein, we report the first photoinduced, phosphine-catalyzed 1,3-carbobromination of allyl carboxylates, affording a range of valuable substituted isopropyl carboxylates (sIPC). The transformation has broad functional group tolerance, is amenable to the late-stage modification of complex molecules and gram-scale synthesis, and expands the reaction profiles of allyl carboxylates and phosphine catalysis. Preliminary experimental and computational studies suggest a non-chain-radical mechanism involving the formation of an electron donor-acceptor complex, 1,2-radical migration (RaM), and Br-atom transfer processes. We anticipate that the 1,2-RaM reactivity of allyl carboxylates and the phosphine-catalyzed radical reaction will both serve as a platform for the development of new transformations in organic synthesis.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.