Dibenzothiophenium
CAS 2244536-10-3, Cat. No EN300-33267752
Reagent for S-, N-, or C-alkynylnation
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 products[2]. The reaction has good tolerance for many functional groups, as an electrophilic reagent it prefers to react with nucleophiles.
Synonyms: 5-(Triisopropylalkynyl) dibenzo[b,d]thiophenium triflate, 5-[2-[tris(1-methylethyl)silyl]ethynyl]-, 1,1,1-trifluoromethanesulfonate (1:1)
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: 10.1002/anie.201807418