ArticleJournal of the American Chemical Society2018
A Practical Electrophilic Nitrogen Source for the Synthesis of Chiral Primary Amines by Copper-Catalyzed Hydroamination.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Modular Access to α-Tertiary Amines: Electrochemical Tandem Di-Functionalization of Olefins With Ammonia Surrogates and Amino Acids.Angewandte Chemie (International ed. in English) · 2026Article
- Catalytic Asymmetric Hydration of Alkenes.Journal of the American Chemical Society · 2026Article
- Mechanistic Insights into the Reductive N-O Bond Cleavage ofACS organic & inorganic Au · 2025Article
- Ni-Catalyzed 1,1- and 1,3-Aminoboration of Unactivated Alkenes.Journal of the American Chemical Society · 2023Article
- NiH-catalyzed anti-Markovnikov hydroamidation of unactivated alkenes with 1,4,2-dioxazol-5-ones for the direct synthesis of N-alkyl amides.Communications chemistry · 2022Article
- The advent of electrophilic hydroxylamine-derived reagents for the direct preparation of unprotected amines.Chemical communications (Cambridge, England) · 2022Review
- Electrophilic Aminating Agents in Total Synthesis.Angewandte Chemie (International ed. in English) · 2021Review
- CuH-Catalyzed Regio- and Enantioselective Hydrocarboxylation of Allenes: Toward Carboxylic Acids with Acyclic Quaternary Centers.Journal of the American Chemical Society · 2021Article
- One tool to bring them all: Au-catalyzed synthesis of B,O- and B,N-doped PAHs from boronic and borinic acids.Chemical science · 2021Article
- Ruthenium-Catalyzed Hydroamination of Unactivated Terminal Alkenes with Stoichiometric Amounts of Alkene and an Ammonia Surrogate by Sequential Oxidation and Reduction.Journal of the American Chemical Society · 2021Article
- Enantioselective Synthesis of β-Amino Acid Derivatives Enabled by Ligand-Controlled Reversal of Hydrocupration Regiochemistry.Angewandte Chemie (International ed. in English) · 2020Article
- CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.Accounts of chemical research · 2020Article
- Diastereo- and Enantioselective CuH-Catalyzed Hydroamination of Strained Trisubstituted Alkenes.ACS catalysis · 2020Article
- Cu-Catalyzed Asymmetric Aminoboration ofOrganic letters · 2019Article
- Asymmetric Synthesis of γ-Amino Alcohols by Copper-Catalyzed Hydroamination.Organic letters · 2019Article
- Cross-Coupling of Heteroatomic Electrophiles.Chemical reviews · 2019Review
- Regio- and Enantioselective Synthesis of 1,2-Diamine Derivatives by Copper-Catalyzed Hydroamination.Organic letters · 2019Article
- Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design.Journal of the American Chemical Society · 2019Article
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3 authors.
Funding
Abstract
A mild and practical method for the catalytic installation of the amino group across alkenes and alkynes has long been recognized as a significant challenge in synthetic chemistry. As the direct hydroamination of olefins using ammonia requires harsh conditions, the development of suitable electrophilic aminating reagents for formal hydroamination methods is of importance. Herein, we describe the use of 1,2-benzisoxazole as a practical electrophilic primary amine source. Using this heterocycle as a new amino group delivery agent, a mild and general protocol for the copper-hydride-catalyzed hydroamination of alkenes and alkynes to form primary amines was developed. This method provides access to a broad range of chiral α-branched primary amines and linear primary amines, as demonstrated by the efficient synthesis of the antiretroviral drug maraviroc and the formal synthesis of several other pharmaceutical agents.
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