ArticleNature communications2020
Cobalt-catalyzed deoxygenative triborylation of allylic ethers to access 1,1,3-triborylalkanes.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed.
- (Poly)Borylated Species as Modern Reactive Groups toward Unusual Synthetic Applications.Angewandte Chemie (International ed. in English) · 2026Review
- High-Throughput Enabled Iridium-Catalyzed C-H Borylation Platform for Late-Stage Functionalization.ACS catalysis · 2025Article
- Tetraborylation ofJACS Au · 2024Article
- Stereodefined polymetalloid alkenes synthesis via stereoselective boron-masking of polyborylated alkenes.Nature communications · 2023Article
- A rapid construction of 1,3,2-benzodiazaborininones [R-B(aam)] from boronic acids and anthranilamides.RSC advances · 2023Article
- Enantioselective Cobalt-Catalyzed Hydroboration of Fluoroalkyl-Substituted Alkenes to Access Chiral Fluoroalkylboronates.Journal of the American Chemical Society · 2022Article
- Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes.Nature communications · 2022Article
- Titanocene(III)-Catalyzed Precision Deuteration of Epoxides.Angewandte Chemie (International ed. in English) · 2022Article
- Article
- Stereoselective Diels-Alder Reactions ofJournal of the American Chemical Society · 2021Article
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4 authors.
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Abstract
Polyborylated organic compounds have been emerging as versatile building blocks in chemical synthesis. Here we report a selective cobalt-catalyzed deoxygenative 1,1,3-triborylation reaction of allylic ethers with pinacolborane to prepare 1,1,3-triborylalkane compounds. With naturally abundant and/or synthetic cinnamic methyl ethers as starting materials, we have achieved the synthesis of a variety of 1,1,3-triborylalkanes (25 examples). The synthetic utility of these 1,1,3-triborylalkanes is demonstrated through site-selective allylation, protodeborylation, and consecutive carbon-carbon bond-forming reactions. Mechanistic studies including deuterium-labeling and control experiments suggest that this 1,1,3-triborylation reaction proceeds through initial cobalt-catalyzed deoxygenative borylation of allylic ethers to form allylic boronates followed by cobalt-catalyzed 1,1-diborylation of the resulting allylic boronates.
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