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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
