ArticleJournal of the American Chemical Society2019
1,2-Boron Shifts of β-Boryl Radicals Generated from Bis-boronic Esters Using Photoredox Catalysis.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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Who cites it
37 citing papers in PubMed.
- Borylcyclopropanes: Synthetic Strategies and Applications.Angewandte Chemie (International ed. in English) · 2026Review
- Copper-Catalyzed Amino Radical Transfer-Mediated Deborylation for Chiral Ester Synthesis.Angewandte Chemie (International ed. in English) · 2026Article
- N-O Dual Functional Group Transposition via Energy Transfer Photocatalysis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- 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
- Strategic 1,n-migration of boronate complexes: a novel platform for remote C-C bond construction.Molecular diversity · 2026Review
- 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
- Overcoming limitations in Chan-Lam amination with alkylboronic esters via aminyl radical substitution.Nature communications · 2025Article
- The Curious Case of β-Boryl Triplet States.Trends in chemistry · 2025Article
- Synthesis of Borylated Orphaned Cyclopropanes through a Boron-Enabled Cycloisomerization Reaction.Journal of the American Chemical Society · 2025Article
- Radical Strategy to the Boron-to-Copper Transmetalation Problem: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
- 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
- A BN-Benzvalene.Journal of the American Chemical Society · 2024Article
- Article
- NHC-Au-Catalyzed Isomerization of Propargylic B(MIDA)s to Allenes and Double Isomerization of Alkynes to 1,3-Dienes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Programmable late-stage functionalization of bridge-substituted bicyclo[1.1.1]pentane bis-boronates.Nature chemistry · 2024Article
- Decarboxylation of β-boryl NHPI esters enables radical 1,2-boron shift for the assembly of versatile organoborons.Nature communications · 2023Article
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4 authors.
Funding
Abstract
1,2-Bis-boronic esters are versatile intermediates that enable the rapid elaboration of simple alkene precursors. Previous reports on their selective mono-functionalization have targeted the most accessible position, retaining the more hindered secondary boronic ester. In contrast, we have found that photoredox-catalyzed mono-deboronation generates primary β-boryl radicals that undergo rapid 1,2-boron shift to form thermodynamically favored secondary radicals, allowing for selective transformation of the more hindered boronic ester. The pivotal 1,2-boron shift, which has been demonstrated to be stereoretentive, enables access to a wide range of functionalized boronic esters and has been applied to highly diastereoselective fragmentation and transannular cyclization reactions. Furthermore, its generality has been shown in a radical cascade reaction with an allylboronic ester.
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Registered trials
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