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CAS 2244536-10-3, Cat. No EN300-33267752
Reagent for S-, N-, or C-alkynylnation

5-(Triisopropylalkynyl) dibenzo[b,d]thiophenium triflate

This extremely useful reagent is designed for S-, N-, or C-alkynylnation in good yields. It is light-yellow crystalline powder, bench-stable for a long time, and well-soluble in DCM (and other similar solvents)1. In the presence of bases such as carbonates, the reagent reacts with thiols, sulfonamides, and doubly activated methylene groups to afford the desired S-, N-, or C-alkynylated products2. The reaction has good tolerance for many functional groups, as an electrophilic reagent it prefers to react with nucleophiles.

Synonyms: dibenzothiophenium; 5-[2-[tris(1-methylethyl)silyl]ethynyl]-, 1,1,1-trifluoromethanesulfonate (1:1); 5-(triisopropylalkynyl) dibenzo[b,d]thiophenium triflate

Selected publication

  1. Preparation of 5-(Triisopropylalkynyl) Dibenzo[b,d]Thiophenium Triflate.

    Waldecker B. Organic Syntheses 2019, 96, 258–276. DOI: 10.15227/orgsyn.096.0258

  2. 5‐(Alkynyl)Dibenzothiophenium Triflates: Sulfur‐Based Reagents for Electrophilic Alkynylation.

    Waldecker B.; Kraft F.; Golz C.; Alcarazo M. Angewandte Chemie International Edition 2018, 57 (38), 12538–12542. DOI: https://doi.org/10.1002/anie.201807418

 

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