ArticleJournal of the American Chemical Society2019
Reactivity Profiles of Diazo Amides, Esters, and Ketones in Transition-Metal-Free C-H Insertion Reactions.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- The concept of Gallium-controlled double C-H functionalization of aliphatic CHNature communications · 2024Article
- Lewis acid mediated allylation of vinyl diazonium ions by allylstannanes.Organic & biomolecular chemistry · 2024Article
- Intramolecular Interception of the Remote Position of Vinylcarbene Silver Complex Intermediates by C(spAngewandte Chemie (International ed. in English) · 2023Article
- Catalytic asymmetric C-H insertion reactions of vinyl carbocations.Science (New York, N.Y.) · 2022Article
- KACS omega · 2020Article
- Substituted α-Alkylidene Cyclopentenones via the Intramolecular Reaction of Vinyl Cations with Alkenes.Organic letters · 2020Article
- Mechanism of Iminium Salt-Catalyzed C(spACS catalysis · 2020Article
- Migratory Aptitudes in Rearrangements of Destabilized Vinyl Cations.The Journal of organic chemistry · 2019Article
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Authors and funding
6 authors.
Funding
Abstract
Vinyl cations derived from diazo ketones participate in transition-metal-free C-H insertion reactions, but the corresponding amide and ester analog exhibit divergent reactivity profiles. Whereas cations formed from diazo ketones undergo a rearrangement and C-H insertion sequence, those from diazo amides do so less efficiently and tend to be competitively trapped before the insertion step occurs. Diazo esters undergo several rearrangement steps and fail to insert. DFT calculations reveal that this disparity stems from two factors: differing levels of electrostatic stabilization of the initially formed vinyl cation by the adjacent carbonyl oxygen and predistortion of the ketone and amide systems toward C-H insertion. The computational data is in strong agreement with experimental results, and this study explains how structural and electronic factors determine the outcome of reactions of diazo carbonyl-derived vinyl cations.
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