ArticleInorganic chemistry2022
Calcium Bistriflimide-Mediated Sulfur(VI)-Fluoride Exchange (SuFEx): Mechanistic Insights toward Instigating Catalysis.
Article in Inorganic chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
What it found
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Who cites it
6 citing papers in PubMed, 20 citations in OpenAlex.
- Substituent Effects on Sulfur Phenolate Exchange Reactions: Reactivity and Bonding Analysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Lewis Acid-Catalyzed Sulfur Fluoride Exchange.Organic letters · 2024Article
- One-Pot Synthesis of Sulfonamides from Unactivated Acids and Amines via Aromatic Decarboxylative Halosulfonylation.Journal of the American Chemical Society · 2023Article
- Synthesis of 2-arylpyridines by the Suzuki-Miyaura cross-coupling of PyFluor with hetero(aryl) boronic acids and esters.Canadian journal of chemistry · 2023Article
- Enantiospecific Synthesis of Aniline-Derived Sulfonimidamides.Organic letters · 2023Article
- Sulfur fluoride exchange.Nature reviews. Methods primers · 2023Article
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
Abstract
We report a mechanistic investigation of calcium bistriflimide-mediated sulfur(VI)-fluoride exchange (SuFEx) between sulfonyl fluorides and amines. We determine the likely pre-activation resting state─a calcium bistriflimide complex with ligated amines─thus allowing for corroborated calculation of the SuFEx activation barrier at ∼21 kcal/mol, compared to 21.5 ± 0.14 kcal/mol derived via kinetics experiments. Transition state analysis revealed: (1) a two-point calcium-substrate contact that activates the sulfur(VI) center and stabilizes the leaving fluoride and (2) a 1,4-diazabicyclo[2.2.2]octane additive that provides Brønsted-base activation of the nucleophilic amine. Stable Ca-F complexes upon sulfonamide formation are likely contributors to inhibited catalytic turnover, and a proof-of-principle redesign provided evidence that sulfonamide formation is feasible with 10 mol % calcium bistriflimide.
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Registered trials
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