ArticleAngewandte Chemie (International ed. in English)2021
Oxidation Under Reductive Conditions: From Benzylic Ethers to Acetals with Perfect Atom-Economy by Titanocene(III) Catalysis.
Article in Angewandte Chemie (International ed. in English), 2021. 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.
- Identification of Ti(salen) Complexes for Efficient Catalysis in Single-Electron Steps by Cyclic Voltammetry.Angewandte Chemie (International ed. in English) · 2025Article
- Article
- Catalytic Asymmetric β-Oxygen Elimination.Angewandte Chemie (International ed. in English) · 2022Article
- Titanocene(III)-Catalyzed Precision Deuteration of Epoxides.Angewandte Chemie (International ed. in English) · 2022Article
- Titanocene-Catalyzed [2+2] Cycloaddition of Bisenones and Comparison with Photoredox Catalysis and Established Methods.Angewandte Chemie (International ed. in English) · 2021Article
- Oxidation Under Reductive Conditions: From Benzylic Ethers to Acetals with Perfect Atom-Economy by Titanocene(III) Catalysis.Angewandte Chemie (International ed. in English) · 2021Article
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5 authors.
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Abstract
Described here is a titanocene-catalyzed reaction for the synthesis of acetals and hemiaminals from benzylic ethers and benzylic amines, respectively, with pendant epoxides. The reaction proceeds by catalysis in single-electron steps. The oxidative addition comprises an epoxide opening. An H-atom transfer, to generate a benzylic radical, serves as a radical translocation step, and an organometallic oxygen rebound as a reductive elimination. The reaction mechanism was studied by high-level dispersion corrected hybrid functional DFT with implicit solvation. The low-energy conformational space was searched by the efficient CREST program. The stereoselectivity was deduced from the lowest lying benzylic radical structures and their conformations are controlled by hyperconjugative interactions and steric interactions between the titanocene catalyst and the aryl groups of the substrate. An interesting mechanistic aspect is that the oxidation of the benzylic center occurs under reducing conditions.
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