Catalytic Alkynylation of Cyclic Acetals and Ketals Enabled by Synergistic Gold(I)/Trimethylsilyl Catalysis
Abstract
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.
Keywords
Ethers
3-Dioxolanes
Alkynylations
Catalytic amounts
Cyclic acetals
Gold acetylide
Regio-selective
Silicon-based
Trimethylsilyl
1
3 dioxolane
acetal derivative
dioxane derivative
gold
Lewis acid
nucleophile
silicon
trimethylsilyl derivative
alkynylation
Article
catalysis
catalyst
quantum yield
reaction analysis
reaction optimization
regioselectivity
ring opening
stereochemistry