ArticleScience (New York, N.Y.)2020
Diverse functionalization of strong alkyl C-H bonds by undirected borylation.
Article in Science (New York, N.Y.), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 68 papers.
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Who cites it
68 citing papers in PubMed.
- Transient Boryl Assistance Enables Stereoselective Alkylation of Acyclic Tetrasubstituted Enolates.Angewandte Chemie (International ed. in English) · 2026Article
- Interpreting terminal selectivity in undirected C(spChemical science · 2026Review
- A tetranuclear nickel hydride cluster capable of reversible activation of aromatic and aliphatic C-H bonds.Nature communications · 2026Article
- Regioselective Amidine-Directed Iridium-Catalyzed C(spOrganic letters · 2026Article
- Terminal-Selective spJournal of the American Chemical Society · 2026Article
- Precise borylation of targeted methyl group via an orderly chain-walking strategy.Science advances · 2026Article
- Pd-Catalyzed C─C Bond Borylation of Biphenylenes Leading to Tri-Ortho-Substituted Biaryls.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Article
- Mapping the Undirected Borylation of C(spJournal of the American Chemical Society · 2026Article
- Transient π-coordination enables nucleophilic borylation of simple arenes.Chemical science · 2026Article
- Electronic Activation Enables the Borylation of Alkyl C-H Bonds in Saturated Nitrogen Heterocycles.Journal of the American Chemical Society · 2025Article
- Regiodivergent α- and β-Functionalization of SaturatedJournal of the American Chemical Society · 2025Article
- Iron-catalyzed aliphatic C-H functionalization to construct carbon-carbon bonds.Nature communications · 2025Article
- Bis-CFACS catalysis · 2025Article
- The Importance of Atomic Charges for Predicting Site-Selective Ir-, Ru-, and Rh-Catalyzed C-H Borylations.The Journal of organic chemistry · 2025Article
- Synthesis of α-substituted cyclic boronatesChemical science · 2025Article
- High-Throughput Enabled Iridium-Catalyzed C-H Borylation Platform for Late-Stage Functionalization.ACS catalysis · 2025Article
- Diversified ring expansion of saturated cyclic amines enabled by azlactone insertion.Nature chemistry · 2024Article
- Atomically precise copper clusters with dual sites for highly chemoselective and efficient hydroboration.Nature communications · 2024Article
- Acridine/Lewis Acid Complexes as Powerful Photocatalysts: A Combined Experimental and Mechanistic Study.ACS catalysis · 2024Article
8 more citing papers are in PubMed but not listed here.
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
The selective functionalization of strong, typically inert carbon-hydrogen (C-H) bonds in organic molecules is changing synthetic chemistry. However, the undirected functionalization of primary C-H bonds without competing functionalization of secondary C-H bonds is rare. The borylation of alkyl C-H bonds has occurred previously with this selectivity, but slow rates required the substrate to be the solvent or in large excess. We report an iridium catalyst ligated by 2-methylphenanthroline with activity that enables, with the substrate as limiting reagent, undirected borylation of primary C-H bonds and, when primary C-H bonds are absent or blocked, borylation of strong secondary C-H bonds. Reactions at the resulting carbon-boron bond show how these borylations can lead to the installation of a wide range of carbon-carbon and carbon-heteroatom bonds at previously inaccessible positions of organic molecules.
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Registered trials
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.