ArticleJournal of the American Chemical Society2016
Nucleophile-Assisted Alkene Activation: Olefins Alone Are Often Incompetent.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 35 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
35 citing papers in PubMed.
- Internally Directed Stereochemical Alteration of Alkene Dihalogenation.The Journal of organic chemistry · 2026Article
- Investigation of olefins as a cocatalyst for halonium catalysis.Chemical communications (Cambridge, England) · 2026Article
- Halide Bond Assisted Double Desymmetrization of Meso-Dicarboxylic Acids with Symmetrical Olefins via Asymmetric Halogenation.Angewandte Chemie (International ed. in English) · 2026Article
- Engineered Flavin-Dependent Halogenases Catalyze C-C Bond Formation via Enantioselective Semipinacol Rearrangement.Journal of the American Chemical Society · 2026Article
- Electrooxidative Divergent Halocyclizations of Ambident Amides.Angewandte Chemie (International ed. in English) · 2026Article
- Stereospecific syn-dichlorination of allylic amines enabled by identification of a superior stereo-directing group.Communications chemistry · 2024Article
- Difunctionalization Processes Enabled by Hexafluoroisopropanol.ACS organic & inorganic Au · 2024Review
- Controlling the regioselectivity of the bromolactonization reaction in HFIP.Chemical science · 2024Article
- Intramolecular chaperone-assisted dual-anchoring activation (ICDA): a suitable preorganization for electrophilic halocyclization.Chemical science · 2024Article
- Alkene Thianthrenation Unlocks Diverse Cation Synthons: Recent Progress and New Opportunities.Angewandte Chemie (International ed. in English) · 2024Review
- Selective C-H Halogenation of Alkenes and Alkynes Using Flavin-Dependent Halogenases.Angewandte Chemie (International ed. in English) · 2024Article
- Ligand effects, solvent cooperation, and large kinetic solvent deuterium isotope effects in gold(I)-catalyzed intramolecular alkene hydroamination.Beilstein journal of organic chemistry · 2024Article
- Asymmetric catalysis by flavin-dependent halogenases.Chirality · 2023Review
- A Catalytic Asymmetric Hydrolactonization.Journal of the American Chemical Society · 2023Article
- Expanding the Reactivity of Flavin Dependent Halogenases Toward Olefins via Enantioselective Intramolecular Haloetherification and Chemoenzymatic Oxidative Rearrangements.ACS catalysis · 2022Article
- Chloride-Mediated Alkene Activation Drives Enantioselective Thiourea and Hydrogen Chloride Co-Catalyzed Prins Cyclizations.Journal of the American Chemical Society · 2022Article
- Lewis Acid-Catalyzed Halonium Generation for Morpholine Synthesis and Claisen Rearrangement.The Journal of organic chemistry · 2022Article
- A Mechanistically Inspired Halenium Ion Initiated Spiroketalization: Entry to Mono- and Dibromospiroketals.Angewandte Chemie (International ed. in English) · 2022Article
- Constrained Dipeptide Surrogates: 5- and 7-Hydroxy Indolizidin-2-one Amino Acid Synthesis from Iodolactonization of Dehydro-2,8-diamino Azelates.Molecules (Basel, Switzerland) · 2021Article
- Are bis(pyridine)iodine(I) complexes applicable for asymmetric halogenation?Organic & biomolecular chemistry · 2021Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
5 authors.
Funding
Abstract
Emerging work on organocatalytic enantioselective halocyclizations naturally draws on conditions where both new bonds must be formed under delicate control, the reaction regime where the concerted nature of the AdE3 mechanism is of greatest importance. Without assistance, many simple alkene substrates react slowly or not at all with conventional halenium donors under synthetically relevant reaction conditions. As demonstrated earlier by Shilov, Cambie, Williams, Fahey, and others, alkenes can undergo a concerted AdE3-type reaction via nucleophile participation, which sets the configuration of the newly created stereocenters at both ends in one step. Herein, we explore the modulation of alkene reactivity and halocyclization rates by nucleophile proximity and basicity, through detailed analyses of starting material spectroscopy, addition stereopreferences, isotope effects, and nucleophile-alkene interactions, all obtained in a context directly relevant to synthesis reaction conditions. The findings build on the prior work by highlighting the reactivity spectrum of halocyclizations from stepwise to concerted, and suggest strategies for design of new reactions. Alkene reactivity is seen to span the range from the often overgeneralized "sophomore textbook" image of stepwise electrophilic attack on the alkene and subsequent nucleophilic bond formation, to the nucleophile-assisted alkene activation (NAAA) cases where electron donation from the nucleophilic addition partner activates the alkene for electrophilic attack. By highlighting the factors that control reactivity across this range, this study suggests opportunities to explain and control stereo-, regio-, and organocatalytic chemistry in this important class of alkene additions.
Indexed as
Identifiers
What OpenQuestion holds
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.