Catalytic Alkynylation of Cyclic Acetals and Ketals Enabled by Synergistic Gold(I)/Trimethylsilyl Catalysis
Résumé
A completely regioselective and challenging gold(I)-catalyzed ring-opening of cyclic 1,3-dioxolanes and dioxanes by trimethylsilyl alkynes to set diol-derived propargyl trimethylsilyl bis-ethers is reported. This unprecedented and not trivial transformation does not operate with the catalytic methodologies recently reported for catalytic alkynylation of acyclic acetals/ketals, and is uniquely enabled by the application of a recently introduced synergistic gold(I)-silicon catalysis concept capable of producing simultaneously catalytic amounts of two key players, a silicon-based Lewis superacid and a nucleophilic gold acetylide. © 2017 American Chemical Society.
Mots clés
- reaction optimization
- Ethers
- 3-Dioxolanes
- Alkynylations
- Catalytic amounts
- Cyclic acetals
- Gold acetylide
- Regio-selective
- Silicon-based
- Trimethylsilyl
- stereochemistry
- ring opening
- regioselectivity
- 1
- reaction analysis
- quantum yield
- catalyst
- catalysis
- Article
- alkynylation
- trimethylsilyl derivative
- silicon
- nucleophile
- Lewis acid
- gold
- dioxane derivative
- acetal derivative
- 3 dioxolane