ArticleAngewandte Chemie (International ed. in English)2022
Photo-Induced Homologation of Carbonyl Compounds for Iterative Syntheses.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 41 citations in OpenAlex.
- Geminal Difunctionalization of Ketones via C─S Bond Insertion of Photogenerated Donor-Donor Diazo Compounds.Angewandte Chemie (International ed. in English) · 2026Article
- Merging photocatalysis with C-H insertions enabled switchable synthesis of indoles and indolines.Nature communications · 2026Article
- On-Target Photoassembly of Pyronin Dyes for Super-Resolution Microscopy.Angewandte Chemie (International ed. in English) · 2025Article
- Facile Access to Hindered Ethers via Photoinduced O-H Bond Insertions.ACS central science · 2025Article
- Visible Light-Induced Reactions of Diazo Compounds and Their Precursors.Chemical reviews · 2024Review
- Photo-cycloaddition reactions of vinyldiazo compounds.Nature communications · 2024Article
- Metal-free photocatalytic cross-electrophile coupling enables C1 homologation and alkylation of carboxylic acids with aldehydes.Nature communications · 2024Article
- Synthesis of substituted benzylboronates by light promoted homologation of boronic acids withChemical science · 2023Article
- Visible-light-induced [3+2] cycloadditions of donor/donor diazo intermediates with alkenes to achieve (spiro)-pyrazolines and pyrazoles.Chemical science · 2023Article
- Photo-Induced Homologation of Carbonyl Compounds for Iterative Syntheses.Angewandte Chemie (International ed. in English) · 2022Article
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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
We describe a photo-induced reaction for the in situ generation of highly reactive alkyl diazo species from carbonyl precursors via photo-excitation of N-tosylhydrazone anions. The diazo intermediates undergo efficient C-H insertion of aldehydes, leading to the productive synthesis of aldehydes and ketones. The method is applicable to the iterative synthesis of densely functionalized carbonyl compounds through sequential trapping of the diazo species with various aldehydes. The reaction proceeds without the need of any catalyst by light irradiation and features high functional group tolerance. More than 70 examples, some performed on a gram-scale, demonstrate the broad applicability of this reaction sequence in synthesis.
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