ArticleOrganometallics2024
Bidentate Phosphine Ligand Impacts on Previously Inaccessible 5-Membered N-Heteroaryne Formation and Functionalization.
Article in Organometallics, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Access to and unexplored reactivity of nickel-bound 5-membered O- and N-heterocyclic arynesChemical science · 2026Article
- Transition Metal-Free Heteroarene Insertion Into C─C Bonds of Benzocyclobutenones.Angewandte Chemie (International ed. in English) · 2026Article
- Synthesis of Unsymmetrical Carbazoles: A Mechanistic Cautionary Tale When UsingACS catalysis · 2026Article
- Ring Expansion via Palladium-Catalyzed Aryne Insertion into C-C Bonds of Benzocyclobutenones.Angewandte Chemie (International ed. in English) · 2025Article
- Bidentate Phosphine Ligand Impacts on Previously Inaccessible 5-Membered N-Heteroaryne Formation and Functionalization.Organometallics · 2024Article
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Authors and funding
4 authors.
Funding
Abstract
5-Membered N-heteroarynes have long been considered synthetically inaccessible; however, we recently reported the use of a bisphosphine-ligated nickel center to stabilize and enable the formation of these otherwise unobtainable intermediates. Motivated by this success, we were compelled to study the role of the ancillary phosphine in aryne formation and reactivity. Herein, a set of four bidentate phosphine ligands with altered phosphine substituents and backbone length are interrogated for their competence as ancillary ligands for 5-membered N-heteroaryne formation. We determined that ligands with phenyl phosphine substituents or linker lengths longer than three carbons were unsuitable for this purpose, while ligands having alkyl phosphine substituents and one, two, or three carbon linkers allowed for successful aryne formation. Reactivity studies using 2-PyZnBr as a nucleophilic coupling partner revealed intriguing regioselectivity enhancement (up to >20:1 r.r.) when utilizing ligands with altered linker lengths. We hypothesize that regioselectivity can be traced back to structural differences between these Ni-aryne complexes, as evidenced by crystallographic characterization.
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