8-{2-[tris(propan-2-yl)silyl]ethynyl}-8-thiatricyclo[7.4.0.0,2,7]trideca-1(13),2,4,6,9,11-hexaen-8-ium trifluoromethanesulfonate

EN300-33267752

Product class

Building Blocks

CAS number

2244536-10-3

MW

514.70

Purity

95%

Stock Availability

US, UA

Lead time

1-5 days delivery time

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)

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

Name:

8-{2-[tris(propan-2-yl)silyl]ethynyl}-8-thiatricyclo[7.4.0.0,2,7]trideca-1(13),2,4,6,9,11-hexaen-8-ium trifluoromethanesulfonate

SMILES:

[O-]S(=O)(=O)C(F)(F)F.CC(C)[Si](C#C[S+]1C2=CC=CC=C2C3=CC=CC=C31)(C(C)C)C(C)C

CAS number:

2244536-10-3

Product class:

Building Blocks

ACD number:

MFCD32672294

Formula:

C₂₄H₂₉F₃O₃S₂Si

Class:

Acetylenes

MW:

514.70

Subclass:

Acetylenes