ArticleJournal of the American Chemical Society2023
Branched-Selective Cross-Electrophile Coupling of 2-Alkyl Aziridines and (Hetero)aryl Iodides Using Ti/Ni Catalysis.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Divergent ring opening and functionalization of N-alkyl aziridines via boryl radical fragmentation.Nature chemistry · 2026Article
- Competition-Derived Relative Reactivity and 3D Electronic-State Analysis of Site- and Facial Selectivity in NaBHJACS Au · 2026Article
- Photoinduced cobalt-catalyzed enantioconvergent synthesis of 1,3-diamines via aziridine ring-opening addition.Science advances · 2026Article
- Nickel-Catalyzed Cross-Electrophile Coupling of Alkynyl Halides With Allylic Acetates.Angewandte Chemie (International ed. in English) · 2026Article
- Development, Application, and Mechanistic Interrogation of a Dual Ni Catalysis Approach to Photoredox-Based C(spJournal of the American Chemical Society · 2025Article
- Nickel-Catalyzed Cross-Dehydrogenative Coupling of Aldehydes and Alkenes toward Skipped Enones.Journal of the American Chemical Society · 2025Article
- Ni/Ti Dual Catalyzed Cross-Electrophile Coupling Between Unactivated Alkyl Chlorides and Aryl Halides.ACS catalysis · 2025Article
- Selective C-N Bond Cleavage in Unstrained Pyrrolidines Enabled by Lewis Acid and Photoredox Catalysis.Journal of the American Chemical Society · 2024Article
- β-Phenethylamine Synthesis: N-Pyridinium Aziridines as Latent Dual Electrophiles.Angewandte Chemie (International ed. in English) · 2024Article
- Green Light Promoted Iridium(III)/Copper(I)-Catalyzed Addition of Alkynes to Aziridinoquinoxalines Through the Intermediacy of Azomethine Ylides.Angewandte Chemie (International ed. in English) · 2024Article
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Authors and funding
3 authors.
Funding
Abstract
The arylation of 2-alkyl aziridines by nucleophilic ring-opening or transition-metal-catalyzed cross-coupling enables facile access to biologically relevant β-phenethylamine derivatives. However, both approaches largely favor C-C bond formation at the less-substituted carbon of the aziridine, thus enabling access to only linear products. Consequently, despite the attractive bond disconnection that it poses, the synthesis of branched arylated products from 2-alkyl aziridines has remained inaccessible. Herein, we address this long-standing challenge and report the first branched-selective cross-coupling of 2-alkyl aziridines with aryl iodides. This unique selectivity is enabled by a Ti/Ni dual-catalytic system. We demonstrate the robustness of the method by a twofold approach: an additive screening campaign to probe functional group tolerance and a feature-driven substrate scope to study the effect of the local steric and electronic profile of each coupling partner on reactivity. Furthermore, the diversity of this feature-driven substrate scope enabled the generation of predictive reactivity models that guided mechanistic understanding. Mechanistic studies demonstrated that the branched selectivity arises from a Ti
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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 Socratic graph.