ArticleJournal of the American Chemical Society2025
Mechanism-Guided Development of Directed C-H Functionalization of Bicyclo[1.1.1]pentanes.
Article in Journal of the American Chemical Society, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Advancing Drug Discovery through Academia-Industry Collaborations: Lessons from Merck Discovery Chemistry Partnerships.ACS central science · 2026Review
- Harnessing Toluene Solvent as a Reactant: Regioselective Benzyl Radical Addition to Multi-π 1,5-Enynes in a Copper-Catalyzed Cascade to Indenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Propellane-free access to bicyclo[1.1.1]pentanes.Nature communications · 2026Review
- Photochemical Construction of Trifluoromethyl Bicyclo[1.1.1]pentyl-heterocycles.Organic letters · 2026Article
- Conformation-driven C3-C(Nature catalysis · 2026Article
- Direct Synthesis of Bicyclo[1.1.1]pentanes by Sequential C═C, C-C Functionalization Reactions.Journal of the American Chemical Society · 2025Article
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
This report describes a detailed study of the palladium-mediated directed C(2)-H functionalization of bicyclo[1.1.1]pentanes (BCPs). Previous attempts to achieve this transformation were reported as unsuccessful. To understand why, a combination of stoichiometric organometallic experiments (to isolate and study the coordination chemistry of these substrates), H/D exchange (to directly probe the C-H activation step), and DFT calculations (to predict optimal directing groups and supporting ligands) was conducted. Collectively, these revealed that cyclometalation at Pd(II) is kinetically facile but thermodynamically unfavorable with aminoquinoline as a directing group and acetonitrile as a supporting ligand. However, changing to a pyridine N-oxide directing group or dimethyl sulfoxide (DMSO) supporting ligand enabled the isolation of stable BCP palladacycles. The functionalization of these complexes was low-yielding with two-electron aryl iodide oxidants. However, moving to single-electron reactions (using in situ-generated aryl radicals) or to electrophilic functionalization (using I
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Registered trials
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