ArticleChemical science2020
Diazaphosphinyl radical-catalyzed deoxygenation of α-carboxy ketones: a new protocol for chemo-selective C-O bond scission
Article in Chemical science, 2020. 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, 30 citations in OpenAlex.
- Secondary Phosphines Bearing N-Heterocyclic Imine Groups: Polarity Umpolung of Highly Electron-Rich P-H Bonds.Inorganic chemistry · 2025Article
- Two Paths to Oxidative C-H Amination Under Basic Conditions: A Theoretical Case Study Reveals Hidden Opportunities Provided by Electron Upconversion.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- 1,3,2-Diazaphospholene-Catalyzed Reductive Cyclizations of Organohalides.Angewandte Chemie (International ed. in English) · 2022Article
- NaMolecules (Basel, Switzerland) · 2022Article
- Review
- Recent progress in reactivity study and synthetic application of N-heterocyclic phosphorus hydrides.National science review · 2021Article
Corrections and comments
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Authors and funding
3 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
C-O bond cleavage is often a key process in defunctionalization of organic compounds as well as in degradation of natural polymers. However, it seldom occurs regioselectively for different types of C-O bonds under metal-free mild conditions. Here we report a facile chemo-selective cleavage of the α-C-O bonds in α-carboxy ketones by commercially available pinacolborane under the catalysis of diazaphosphinane based on a mechanism switch strategy. This new reaction features high efficiency, low cost and good group-tolerance, and is also amenable to catalytic deprotection of desyl-protected carboxylic acids and amino acids. Mechanistic studies indicated an electron-transfer-initiated radical process, underlining two crucial steps: (1) the initiator azodiisobutyronitrile switches originally hydridic reduction to kinetically more accessible electron reduction; and (2) the catalytic phosphorus species upconverts weakly reducing pinacolborane into strongly reducing diazaphosphinane.
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Registered trials
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