CAS 181934-30-5, Cat. No EN300-152972
Reagent for alkynylation
1-[(Triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) is a hypervalent iodine-based alkynylation reagent used for metal-free C–H alkynylation1–3. It enables the direct alkynylation of aldehydes to ynones under mild conditions. The reagent also facilitates thiol alkynylation, forming thioalkynes valuable for bioconjugation. Additionally, it allows decarboxylative alkynylation of carboxylic acids via photoredox catalysis4. Bench-stable and moisture-tolerant, the reagent provides a scalable and practical solution for synthetic, medicinal, and material chemistry.
Synonyms: 1,2-benziodoxol-3(1H)-one, 1-[[tris(1-methylethyl)silyl]ethynyl]-; 1-((tris(1-methylethyl)silyl)ethynyl)-1,2-benziodoxol-3(1H)-one; 1-[2-tri(propan-2-yl)silylethynyl]-1lambda3,2-benziodoxol-3-one; 1-((triisopropylsilyl)ethynyl)-1,2-benziodoxol-3(1H)-one; 1-{[tris-(1-methylethyl)silyl]ethynyl]}-1,2-benziodoxol-3(1H)-one; 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one
Selected publications
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Highly Chemoselective and Practical Alkynylation of Thiols.
Frei R.; Waser J. J Am Chem Soc 2013, 135 (26), 9620–9623. DOI: 10.1021/ja4044196
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Radical-Induced Metal-Free Alkynylation of Aldehydes by Direct C-H Activation.
Liu X.; Yu L.; Luo M.; Zhu J.; Wei W. Chemistry - A European Journal 2015, 21 (24), 8745–8749. DOI: 10.1002/chem.201501094
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Silyl Ethynyl Benziodoxolone Reagents.
González D. F.; Nicolai S.; Waser J.; Le Vaillant F. Encyclopedia of Reagents for Organic Synthesis 2019, 1–14. DOI: 10.1002/047084289X.rn01503.pub2
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Room‐Temperature Decarboxylative Alkynylation of Carboxylic Acids Using Photoredox Catalysis and EBX Reagents.
Le Vaillant F.; Courant T.; Waser J. Angewandte Chemie 2015, 127 (38), 11352–11356. DOI: 10.1002/ange.201505111