ArticleJournal of the American Chemical Society2021
Synthesis of Pyrroles via Consecutive 6π-Electrocyclization/Ring-Contraction of Sulfilimines.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 29 citations in OpenAlex.
- Sulfur-Directed Construction of Vinyl Cyclopropanes from 1,3-Dienes.Angewandte Chemie (International ed. in English) · 2026Article
- Thiophene Derivatives as Versatile Precursors for (Hetero)Arene and Natural Product Synthesis.Angewandte Chemie (International ed. in English) · 2026Review
- Copper(I)-nitrene platform for chemoproteomic profiling of methionine.Nature communications · 2024Article
- Ring expansion of indene by photoredox-enabled functionalized carbon-atom insertion.Nature catalysis · 2024Article
- Scaffold hopping by net photochemical carbon deletion of azaarenes.Science (New York, N.Y.) · 2022Article
- Mechanistic Insights into the Formation of 1-Alkylidene/Arylidene-1,2,4-triazolinium Salts: A Combined NMR/Density Functional Theory Approach.The Journal of organic chemistry · 2022Article
- Ti-Catalyzed and -Mediated Oxidative Amination Reactions.Accounts of chemical research · 2021Article
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Authors and funding
9 authors at 1 institution in 1 country.
Funding
Abstract
We present a modular, synthetic entry to polysubstituted pyrroles employing readily available 2,5-dihydrothiophenes. Ring-opening of the heterocycle provides access to a panel of 1,3-dienes which undergo pyrrole formation in the presence of inexpensive chloramine-T trihydrate. The transformation is conducted in an open flask and proceeds at ambient temperatures (23 °C) in nondry solvents. A careful adjustment of the electronics and sterics of the 1,3-diene precursor allows for the isolation of key intermediates. DFT studies identified a reaction mechanism that features a 6π-electrocyclization of a sulfilimine intermediate followed by spontaneous ring-contraction to reveal the pyrrole skeleton.
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Registered trials
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