ArticleACS catalysis2019
Cu-Catalyzed Hydroboration of Benzylidenecyclopropanes: Reaction Optimization, (Hetero)Aryl Scope, and Origins of Pathway Selectivity.
Article in ACS catalysis, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
What it found
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Who cites it
8 citing papers in PubMed.
- Borylcyclopropanes: Synthetic Strategies and Applications.Angewandte Chemie (International ed. in English) · 2026Review
- The current utility and future potential of multiborylated alkanes.Nature reviews. Chemistry · 2024Review
- Enantio- and Regioselective Cascade Hydroboration of Methylenecyclopropanes for Facile Access to Chiral 1,3- and 1,4-Bis(boronates).Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Copper catalyzed borocarbonylation of benzylidenecyclopropanes through selective proximal C-C bond cleavage: synthesis of γ-boryl-γ,δ-unsaturated carbonyl compounds.Chemical science · 2022Article
- Catalyst-controlled selective borocarbonylation of benzylidenecyclopropanes: regiodivergent synthesis of γ-vinylboryl ketones and β-cyclopropylboryl ketones.Chemical science · 2022Article
- Hydroboration of Terminal Alkenes andAngewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2021Article
- Hydroboration of Terminal Alkenes and trans-1,2-Diboration of Terminal Alkynes Catalyzed by a Manganese(I) Alkyl Complex.Angewandte Chemie (International ed. in English) · 2021Article
- Multifaceted Substrate-Ligand Interactions Promote the Copper-Catalyzed Hydroboration of Benzylidenecyclobutanes and Related Compounds.ACS catalysis · 2020Article
Corrections and comments
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Authors and funding
17 authors.
Funding
Abstract
The copper-catalyzed hydroboration of benzylidenecyclopropanes, conveniently accessed in one step from readily available benzaldehydes, is reported. Under otherwise identical reaction conditions, two distinct phosphine ligands grant access to different products by either suppressing or promoting cyclopropane opening via β-carbon elimination. Computational studies provide insight into how the rigidity and steric environment of these different bis-phosphine ligands influence the relative activation energies of β-carbon elimination versus protodecupration from the key benzylcopper intermediate. The method tolerates a wide variety of heterocycles prevalent in clinical and pre-clinical drug development, giving access to valuable synthetic intermediates. The versatility of the tertiary cyclopropylboronic ester products is demonstrated through several derivatization reactions.
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