ArticleOrganic letters2019
Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions.
Article in Organic letters, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed, 24 citations in OpenAlex.
- Effects of acupuncture on brain functional networks in patients with mild cognitive impairment and Alzheimer's disease: a systematic review and activation likelihood estimation meta-analysis of neuroimaging studies.Quantitative imaging in medicine and surgery · 2026Article
- Zinc-Catalyzed Cyclization of Alkynyl Derivatives: Substrate Scope and Mechanistic Insights.Inorganic chemistry · 2024Article
- Synthesis of Diversified Pyrazolo[3,4-Molecules (Basel, Switzerland) · 2022Article
- Interrupted Curtius Rearrangements of Quaternary Proline Derivatives: A Flow Route to Acyclic Ketones and Unsaturated Pyrrolidines.The Journal of organic chemistry · 2021Article
- Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions.Molecules (Basel, Switzerland) · 2021Article
- The Formosalides: Structure Determination by Total Synthesis.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization of the alkyne that leads to preferential heteroatom attack at the more electron-deficient carbon. The electronic effects are studied in other contexts, including hydroacyloxylation and hydroamination, and similar trends in directionality are predominant although not uniformly observed.
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