Synthesis of β-Dicarbonylated Tetrahydropiperidines via Direct Oxidative Cross-Coupling between Different C(sp)-H Bonds.

Clicks: 298
ID: 79142
2020
Article Quality & Performance Metrics
Overall Quality
Not rated
Combines reader engagement with the AI quality analysis. This article has not been analysed, so there is no overall score — reader engagement is measured and shown alongside.
AI Quality Assessment
Not analyzed
Readership in this journal
Emerging

Ranked #30 of 103 articles by views in The Journal of organic chemistry

Most read Least read

Bar heights use a square-root scale.

Mint this article as an NFT
Not yet minted

Create a permanent, verifiable on-chain record of this article on the Scimatic Network. The NFT is held in your Journament account, and you can withdraw it to your own wallet at any time.

5 SUSD one-off · no wallet required
Sign in to mint
Abstract
A novel and convenient synthesis of β-dicarbonylated tetrahydropiperidines from the cascade reactions of piperidine derivatives with methyl ketones is presented. Mechanistically, the formation of the title compounds involves a hitherto unreported oxidative cross-coupling between different C(sp)-H bonds through the in situ generation of a cyclic enamine and an α-keto radical as the key intermediates followed by their radical addition and further oxidation of the addition adduct. To our knowledge, this is the first example in which β-dicarbonyl-substituted tetrahydropiperidines were prepared using readily available saturated cyclic amines as substrates and inexpensive and ubiquitous methyl ketones as dicarbonylation reagents. In addition, the product thus obtained could be easily transformed into structurally and pharmaceutically interesting polycyclic compounds in good efficiency.
Reference Key
wang2020synthesisthe Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Wang, Fang;Zhang, Xinying;He, Yan;Fan, Xuesen;
Journal The Journal of organic chemistry
Year 2020
DOI
10.1021/acs.joc.9b02924
URL
Keywords
layered double hydroxide flame retardancy cellulose aerogel smoke suppression

Citations

No citations found. To add a citation, contact the admin at info@scimatic.org

Comments

No comments yet. Be the first to comment on this article.