ArticleACS catalysis2022
Amine Organocatalysis of Remote, Chemoselective C(sp
Article in ACS catalysis, 2022. 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, 21 citations in OpenAlex.
- Fluorinated Solvents for Chemoselective Oxidations: A Strategy toward Synthetic Ideality in Natural Product Synthesis.ACS organic & inorganic Au · 2026Article
- Biosynthesis of the Antifungal Polyhydroxy-Polyketide Acrophialocinol.Organic letters · 2025Article
- Organocatalytic activation of hydrogen peroxide: towards green and sustainable oxidations.Chemical science · 2024Review
- Radical and Cationic Pathways in C(Journal of the American Chemical Society · 2023Article
- Highly Selective C(spJournal of the American Chemical Society · 2023Article
- A preparative small-molecule mimic of liver CYP450 enzymes in the aliphatic C-H oxidation of carbocyclicProceedings of the National Academy of Sciences of the United States of America · 2023Article
- Peracid Oxidation of Unactivated spChemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Redox-active molecules as organocatalysts for selective oxidative transformations - an unperceived organocatalysis field.Beilstein journal of organic chemistry · 2022Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
We introduce an organocatalytic approach for oxaziridinium-mediated C-H hydroxylation that employs secondary amines as catalysts. We also demonstrate the advantages of this operationally simple catalytic strategy for achieving high yielding and highly selective remote hydroxylation of compounds bearing oxidation-sensitive functional groups such as alcohols, ethers, carbamates, and amides. By employing hexafluoroisopropanol as the solvent in the absence of water, a proposed hydrogen bonding effect leads to, among other advantages, as high as ≥99:1 chemoselectivity for remote aliphatic hydroxylation of 2° alcohols, an otherwise unsolved synthetic challenge normally complicated by substantial amounts of alcohol oxidation. Initial studies of the reaction mechanism indicate the formation of an oxaziridinium salt as the active oxidant, and a C-H oxidation step that proceeds in a stereospecific manner via concerted insertion or hydrogen atom transfer/radical rebound. Furthermore, preliminary results indicate that site selectivity can be affected by amine catalyst structure. In the long term, we anticipate that this will enable new strategies for catalyst control of selectivity based on the abundance of catalytic scaffolds that have proliferated over the last twenty years as a result of Nobel Prize-winning discoveries.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.