Maintenance Notice (4:30 AM - 11:00 AM December 21, 2024): This website is scheduled to be unavailable due to maintenance. We appreciate your patience and understanding.
Published TCIMAIL newest issue No.197
Maximum quantity allowed is 999
Merci de sélectionner la quantité
A Mild Ethynylating Reagent
1-[(Triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (=TIPS-EBX) is a mild ethynylating reagent and well used for site-selective ethynylations. For example, a palladium catalyzed ethynylation of indoles proceeds at C2-selectively, while complementary C3-selective ethynylation is accomplished by using gold chloride as a catalyst. Gold catalyst-promoted site-selective ethynylations are applied to thiophenes and N,N-dialkyl anilines affording C2-ethynylated thiophenes and para-ethynylated anilines. A TIPS group on the alkynes can be easily removed under basic conditions and affords related terminal alkynes. Thus, TIPS-EBX is an efficient ethynylating reagent applicable for click chemistry and material sciences.
References
- Synthesis of 1-[(triisopropylsilyl)ethynyl]-1λ3,2-benziodoxol-3(1H)-one and alkynylation of indoles, thiophenes, and anilines
- C2-Selective direct alkynylation of indoles
- Direct alkynylation of indole and pyrrole heterocycles
- Direct alkynylation of thiophenes: cooperative activation of TIPS–EBX with gold and Brø";"nsted acids
- Para-selective gold-catalyzed direct alkynylation of anilines
