ArticleAngewandte Chemie (International ed. in English)2018
Trimethylsilyl-Protected Alkynes as Selective Cross-Coupling Partners in Titanium-Catalyzed [2+2+1] Pyrrole Synthesis.
Article in Angewandte Chemie (International ed. in English), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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34 citing papers in PubMed, 103 citations in OpenAlex.
- Catalytic Sulfur-Atom Transfer Enabled by a Bis(disulfide) Titanium Complex.Angewandte Chemie (International ed. in English) · 2026Article
- Upcycling Silicon as Heterogeneous Palladium Catalysts: Heck-Cassar Cross-Coupling in Batch and Flow Conditions.ChemSusChem · 2026Article
- A General Strategy for the Synthesis of Jerangolids Enabled by π-allyl Stille Coupling.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Regioselective Stepwise Synthesis of Unsymmetrical 1,2,5-Triarylpyrroles via Palladium-Catalyzed Decarboxylative Cross-Coupling and C-H Arylation.Molecules (Basel, Switzerland) · 2026Article
- Alkyne Carboamination with Imines Catalyzed by [pyOrganometallics · 2025Article
- Ti-Catalyzed Oxidative Amination Using Anilines.ACS catalysis · 2024Article
- Review
- Evaluation of Tungsten Catalysis among Early Transition Metals forInorganic chemistry · 2024Article
- Molecular Editing of Pyrroles via a Skeletal Recasting Strategy.ACS central science · 2023Article
- Synthesis of Ti Complexes Supported by an ortho-terphenoxide Ligand and their Applications in Alkyne Hydroamination Catalysis.Organometallics · 2023Article
- Ti-Catalyzed Multicomponent Synthesis of Pyrroles Using Allene Coupling Partners.Organometallics · 2023Article
- Selective propargylic C(spChemical science · 2021Article
- Marine Pyrrole Alkaloids.Marine drugs · 2021Review
- Ti-Catalyzed and -Mediated Oxidative Amination Reactions.Accounts of chemical research · 2021Article
- Multicomponent syntheses of 5- and 6-membered aromatic heterocycles using group 4-8 transition metal catalysts.Chemical science · 2021Review
- Iron-Catalyzed Vinylsilane Dimerization and Cross-Cycloadditions with 1,3-Dienes: Probing the Origins of Chemo- and Regioselectivity.ACS catalysis · 2021Article
- A Mononuclear and High-Spin Tetrahedral TiInorganic chemistry · 2020Article
- Synthesis of pentasubstituted 2-aryl pyrroles from boryl and stannyl alkynesChemical science · 2020Article
- Retracted Article: Metal-free [2+2+1] cycloaddition polymerization of alkynes, nitriles, and oxygen atoms to functional polyoxazoles.RSC advances · 2020Article
- Ti-catalyzed ring-opening oxidative amination of methylenecyclopropanes with diazenes.Chemical science · 2020Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Trimethylsilyl (TMS)-protected alkynes served as selective alkyne cross-coupling partners in titanium-catalyzed [2+2+1] pyrrole synthesis. Reactions of TMS-protected alkynes with internal alkynes and azobenzene under the catalysis of titanium imido complexes yielded pentasubstituted 2-TMS-pyrroles with greater than 90 % selectivity over the other nine possible pyrrole products. The steric and electronic effects of the TMS group were both identified to play key roles in this highly selective pyrrole synthesis. This strategy provides a convenient method to synthesize multisubstituted pyrroles as well as an entry point for further pyrrole diversification through facile modification of the resulting 2-silyl pyrrole products, as demonstrated through a short formal synthesis of the marine natural product lamellarin R.
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