ArticleJournal of the American Chemical Society2014
A new tool to guide halofunctionalization reactions: the halenium affinity (HalA) scale.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed.
- Electrochemically cooperative halogen-cation delivery enables modular electrophilic haloesterification of both activated and unactivated alkenes.Chemical science · 2026Article
- Investigation of olefins as a cocatalyst for halonium catalysis.Chemical communications (Cambridge, England) · 2026Article
- Engineered Flavin-Dependent Halogenases Catalyze C-C Bond Formation via Enantioselective Semipinacol Rearrangement.Journal of the American Chemical Society · 2026Article
- Computational tools for the prediction of site- and regioselectivity of organic reactions.Chemical science · 2025Review
- Identifying and Engineering Flavin Dependent Halogenases for Selective Biocatalysis.Accounts of chemical research · 2024Article
- Intramolecular chaperone-assisted dual-anchoring activation (ICDA): a suitable preorganization for electrophilic halocyclization.Chemical science · 2024Article
- Selective C-H Halogenation of Alkenes and Alkynes Using Flavin-Dependent Halogenases.Angewandte Chemie (International ed. in English) · 2024Article
- Biomimetic chlorine-induced polyene cyclizations harnessing hypervalent chloroiodane-HFIP assemblies.Chemical science · 2023Article
- Total Synthesis and Structure Confirmation of (Organic letters · 2022Article
- The Single-Component Flavin Reductase/Flavin-Dependent Halogenase AetF is a Versatile Catalyst for Selective Bromination and Iodination of Arenes and Olefins.Angewandte Chemie (International ed. in English) · 2022Article
- Analysis of Laboratory-Evolved Flavin-Dependent Halogenases Affords a Computational Model for Predicting Halogenase Site Selectivity.Chem catalysis · 2022Article
- Catalytic Chemo-, Regio-, Diastereo-, and Enantioselective Bromochlorination of Unsaturated Systems Enabled by Lewis Base-Controlled Chloride Release.Journal of the American Chemical Society · 2022Article
- Enantioselective Inter- and Intramolecular Sulfenofunctionalization of Unactivated Cyclic and (ACS catalysis · 2022Article
- A Mechanistically Inspired Halenium Ion Initiated Spiroketalization: Entry to Mono- and Dibromospiroketals.Angewandte Chemie (International ed. in English) · 2022Article
- Halonium Catalysis: An Underutilized and Underexplored Catalytic Concept in Olefin Functionalizations.Synlett : accounts and rapid communications in synthetic organic chemistry · 2021Article
- Ritter-enabled catalytic asymmetric chloroamidation of olefins.Chemical science · 2020Article
- Catalytic, Enantioselective Sulfenofunctionalization of Alkenes: Development and Recent Advances.Angewandte Chemie (International ed. in English) · 2020Review
- Site-Selective C-H Halogenation Using Flavin-Dependent Halogenases Identified via Family-Wide Activity Profiling.ACS central science · 2019Article
- Understanding and Improving the Activity of Flavin-Dependent Halogenases via Random and Targeted Mutagenesis.Annual review of biochemistry · 2018Review
- Absolute and relative facial selectivities in organocatalytic asymmetric chlorocyclization reactions.Chemical science · 2018Article
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Authors and funding
6 authors.
Funding
Abstract
We introduce a previously unexplored parameter-halenium affinity (HalA)- as a quantitative descriptor of the bond strengths of various functional groups to halenium ions. The HalA scale ranks potential halenium ion acceptors based on their ability to stabilize a "free halenium ion". Alkenes in particular but other Lewis bases as well, such as amines, amides, carbonyls, and ether oxygen atoms, etc., have been classified on the HalA scale. This indirect approach enables a rapid and straightforward prediction of chemoselectivity for systems involved in halofunctionalization reactions that have multiple nucleophilic sites. The influences of subtle electronic and steric variations, as well as the less predictable anchimeric and stereoelectronic effects, are intrinsically accounted for by HalA computations, providing quantitative assessments beyond simple "chemical intuition". This combined theoretical-experimental approach offers an expeditious means of predicting and identifying unprecedented reactions.
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