ArticleAngewandte Chemie (International ed. in English)2022
Dual Nickel/Photoredox-Catalyzed Site-Selective Cross-Coupling of 1,2-Bis-Boronic Esters Enabled by 1,2-Boron Shifts.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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17 citing papers in PubMed, 54 citations in OpenAlex.
- Converting 1,1-Bisborylalkanes into 1,2-Bisborylalkanes Enabled by Iron Ligand-to-Metal Charge Transfer (LMCT) Photocatalysis.Angewandte Chemie (International ed. in English) · 2026Article
- Radical 1,2-boron shift in modern organoboron synthesis.Frontiers in chemistry · 2026Review
- Functional Group Transposition Enabled by Palladium and Photo Dual Catalysis.Journal of the American Chemical Society · 2025Article
- The Curious Case of β-Boryl Triplet States.Trends in chemistry · 2025Article
- Rapid Methylation of Aryl Bromides Using Air-Stable DABCO-Bis(Trimethylaluminum) via Nickel Metallaphotoredox Catalysis.Angewandte Chemie (International ed. in English) · 2025Article
- Asymmetric synthesis of β-amino acid derivatives by stereocontrolled C(spNature communications · 2025Article
- Synthesis of Borylated Orphaned Cyclopropanes through a Boron-Enabled Cycloisomerization Reaction.Journal of the American Chemical Society · 2025Article
- Borylated strain rings synthesis via photorearrangements enabled by energy transfer catalysis.Nature communications · 2025Article
- Development of N-centered radical scavengers that enables photoredox-catalyzed transition-metal-free radical amination of alkyl pinacol boronates.Nature communications · 2025Article
- Photosynthesis of AuNature communications · 2024Article
- The current utility and future potential of multiborylated alkanes.Nature reviews. Chemistry · 2024Review
- Site-Selective Activation and Stereospecific Functionalization of Bis(boronic Esters) Derived from 2-Alkenes: Construction of Propionates and Other 1,2-Difunctional Motifs.Angewandte Chemie (International ed. in English) · 2024Article
- Article
- Decarboxylation of β-boryl NHPI esters enables radical 1,2-boron shift for the assembly of versatile organoborons.Nature communications · 2023Article
- Enantioselective Suzuki cross-coupling of 1,2-diboryl cyclopropanes.Chemical science · 2023Article
- 1,2-Radical Shifts in Photoinduced Synthetic Organic Transformations: A Guide to the Reactivity of Useful Radical Synthons.ACS organic & inorganic Au · 2022Review
- Dual Nickel/Photoredox-Catalyzed Site-Selective Cross-Coupling of 1,2-Bis-Boronic Esters Enabled by 1,2-Boron Shifts.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
4 authors at 1 institution in 2 countries.
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No grant is acknowledged in the PubMed record.
Abstract
Site-selective transition-metal-catalyzed mono-deboronative cross-couplings of 1,2-bis-boronic esters are valuable methods for the synthesis of functionalized organoboron compounds. However, such cross-couplings are limited to reaction of the sterically less hindered primary boronic ester. Herein, we report a nickel/photoredox-catalyzed mono-deboronative arylation of 1,2-bis-boronic esters that is selective for coupling of the more sterically hindered secondary/tertiary position. This is achieved by taking advantage of a 1,2-boron shift of primary β-boryl radicals to the thermodynamically favored secondary/tertiary radicals, which are subsequently intercepted by the nickel catalyst to enable arylation. The mild conditions are amenable to a broad range of aryl halides to give β-aryl boronic ester products in good yields and with high regioselectivity. This method also allows stereodivergent coupling of cyclic cis-1,2-bis-boronic esters to give trans-substituted products.
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