ArticleJournal of the American Chemical Society2012
Copper-catalyzed intramolecular alkene carboetherification: synthesis of fused-ring and bridged-ring tetrahydrofurans.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed, 166 citations in OpenAlex.
- Copper-Catalyzed Cyclization and Alkene Transposition Cascade Enables a Modular Synthesis of Complex Spirocyclic Ethers.Journal of the American Chemical Society · 2025Article
- Photoinduced β-fragmentation of aliphatic alcohol derivatives for forging C-C bonds.Nature communications · 2022Article
- Asymmetric radical carboesterification of dienes.Nature communications · 2021Article
- Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers.Chemical communications (Cambridge, England) · 2021Article
- Copper-Catalyzed Three-Component Alkene Carbofunctionalization: C-N, C-O, and C-C Bond Formation from a Single Reaction Platform.Organic letters · 2021Article
- Visible Light Promoted, Catalyst-Free Radical Carbohydroxylation and Carboetherification under Mild Biomimetic Conditions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Copper-catalyzed enantioselective synthesis of bridged bicyclic ketals from 1,1-disubstituted-4-methylene-1,6-hexanediols and related alkenols.Chemical communications (Cambridge, England) · 2021Article
- Catalytic generation of alkoxy radicals from unfunctionalized alcohols.Chemical science · 2020Review
- Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers.Organic letters · 2020Article
- Enantioselective, Aerobic Copper-Catalyzed Intramolecular Carboamination and Carboetherification of Unactivated Alkenes.ACS catalysis · 2020Article
- Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer.Angewandte Chemie (International ed. in English) · 2020Article
- Electrochemical oxidation-induced etherification via C(spScience advances · 2020Article
- Synthesis of Spirocyclic Ethers by Enantioselective Copper-Catalyzed Carboetherification of Alkenols.Angewandte Chemie (International ed. in English) · 2018Article
- Selenide-catalyzed enantioselective synthesis of trifluoromethylthiolated tetrahydronaphthalenes by merging desymmetrization and trifluoromethylthiolation.Nature communications · 2018Article
- First-Row Late Transition Metals for Catalytic Alkene Hydrofunctionalisation: Recent Advances in C-N, C-O and C-P Bond Formation.Molecules (Basel, Switzerland) · 2017Review
- Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes.The Journal of organic chemistry · 2017Article
- Catalytic, Stereoselective Dihalogenation of Alkenes: Challenges and Opportunities.Angewandte Chemie (International ed. in English) · 2015Review
- Development of Enantioselective Palladium-Catalyzed Alkene Carboalkoxylation Reactions for the Synthesis of Tetrahydrofurans.Angewandte Chemie (International ed. in English) · 2015Article
- Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes.Journal of the American Chemical Society · 2015Article
- Tandem C-H oxidation/cyclization/rearrangement and its application to asymmetric syntheses of (-)-brussonol and (-)-przewalskine E.Nature communications · 2015Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Fused-ring and bridged-ring tetrahydrofuran scaffolds are found in a number of natural products and biologically active compounds. A new copper-catalyzed intramolecular carboetherification of alkenes for the synthesis of bicyclic tetrahydrofurans is reported herein. The reaction involves Cu-catalyzed intramolecular addition of alcohols to unactivated alkenes and subsequent aryl C-H functionalization provides the C-C bond. Mechanistic studies indicate a primary carbon radical intermediate is involved and radical addition to the aryl ring is the likely C-C bond-forming mechanism. Preliminary catalytic enantioselective reactions are promising (up to 75% ee) and provide evidence that copper is involved in the alkene addition step, likely through a cis-oxycupration mechanism. Catalytic enantioselective alkene carboetherification reactions are rare and future development of this new method into a highly enantioselective process is promising. During the course of the mechanistic studies a protocol for alkene hydroetherification was also developed.
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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.