ArticleThe Journal of organic chemistry2020
Nickel-Catalyzed Three-Component Cycloadditions of Enoates, Alkynes, and Aldehydes.
Article in The Journal of organic chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Mechanistic insights on C(acyl)-N functionalisation mediated by late transition metals.Dalton transactions (Cambridge, England : 2003) · 2024Review
- Stereospecific Nickel-Catalyzed Cross-Electrophile Coupling Reaction of Alkyl Mesylates and Allylic Difluorides to Access Enantioenriched Vinyl Fluoride-Substituted Cyclopropanes.ACS catalysis · 2023Article
- Activation Mechanism of Nickel(0)Organometallics · 2022Article
- Case Study of N-Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
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Authors and funding
4 authors.
Funding
Abstract
A method for the three-component cycloaddition of enoates, alkynes, and aldehydes has been developed. Building upon previous work by this group in which stoichiometrically generated metallacycles undergo alkylation, we report a catalytic, alkylative [3 + 2] cycloaddition. From simple starting materials, structurally complex cyclopentenones may be rapidly assembled. Computational investigation of the mechanism (ωB97X-D3/cc-pVTZ//ωB97X/6-31G(d)) identified three energetically feasible pathways. Based on the relative rates of ketene formation compared to isomerization to a seven-membered metallacycle, the most likely mechanism has been determined to occur "ketene-first", with carbocyclization prior to aldol addition. Deuterium labeling studies suggest that formation of the seven-membered metallacycle becomes possible when an α-substituted enoate is used. This observed change in selectivity is due to the increased difficulty of phenoxide elimination with the inclusion of additional steric bulk of the α-substituent. The net transformation results in a [3 + 2] cycloaddition accompanied by an alkylation of the enoate substituent.
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