ArticleJournal of the American Chemical Society2023
Convergent Deboronative and Decarboxylative Phosphonylation Enabled by the Phosphite Radical Trap "BecaP".
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 13 papers.
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Who cites it
13 citing papers in PubMed, 52 citations in OpenAlex.
- Direct photochemical activation of aliphatic carboxylic acids toward phosphinylationChemical science · 2026Article
- Cobalt-catalyzed Markovnikov-selective hydrophosphonylation of unactivated alkenes enabled by phthalimidyl phosphite reagents.Nature communications · 2026Article
- Redirecting radical phosphonylation via energy-transfer-enabled diradical rearrangement.Science advances · 2026Article
- Iron-Photocatalyzed C(spAngewandte Chemie (International ed. in English) · 2026Article
- Converting 1,1-Bisborylalkanes into 1,2-Bisborylalkanes Enabled by Iron Ligand-to-Metal Charge Transfer (LMCT) Photocatalysis.Angewandte Chemie (International ed. in English) · 2026Article
- Catalytic Markovnikov hydrophosphorylation of unactivated olefins via a radical-polar crossover rearrangement.Nature communications · 2026Article
- Deoxygenative phosphonation of ketones by titanium.Chemical science · 2026Article
- Direct deoxygenative arylation of saccharides via phosphorus-assisted C-OH bond activation.Nature communications · 2025Article
- Small Molecule Catalyst for Peptide Synthesis.Journal of the American Chemical Society · 2025Article
- Photochemical phosphorus-enabled scaffold remodeling of carboxylic acids.Science (New York, N.Y.) · 2024Article
- Development of a General Organophosphorus Radical Trap: Deoxyphosphonylation of Alcohols.Journal of the American Chemical Society · 2024Article
- The key phosphorus moieties in drug design: antimicrobials and beyond.Future medicinal chemistry · 2024Article
- Synthesis of tertiary alkylphosphonate oligonucleotides through light-driven radical-polar crossover reactions.Nature communications · 2023Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Carbon-phosphorus bond formation is significant in synthetic chemistry because phosphorus-containing compounds offer numerous indispensable biochemical roles. While there is a plethora of methods to access organophosphorus compounds, phosphonylations of readily accessible alkyl radicals to form aliphatic phosphonates are rare and not commonly used in synthesis. Herein, we introduce a novel phosphorus radical trap "BecaP" that enables facile and efficient phosphonylation of alkyl radicals under visible light photocatalytic conditions. Importantly, the ambiphilic nature of BecaP allows redox neutral reactions with both nucleophilic (activated by single-electron oxidation) and electrophilic (activated by single-electron reduction) alkyl radical precursors. Thus, a broad scope of feedstock alkyl potassium trifluoroborate salts and redox active carboxylate esters could be employed, with each class of substrate proceeding through a distinct mechanistic pathway. The mild conditions are applicable to the late-stage installation of phosphonate motifs into medicinal agents and natural products, which is showcased by the straightforward conversion of baclofen (muscle relaxant) to phaclofen (GABA
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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.