Silver-Catalyzed [2 + 2] Cycloadditions of Siloxy Alkynes
Journal of the American Chemical Society2004Vol. 126(24), pp. 7442–7443
Citations Over TimeTop 10% of 2004 papers
Abstract
We have described the first [2 + 2] cycloadditions of siloxy alkynes with a range of unsaturated carbonyl compounds. The reactions are efficiently promoted by substoichiometric amount of silver trifluoromethanesulfonimide and display excellent regio- and diastereoselectivity combined with a broad substrate scope. Our studies have established unambiguously the stepwise mechanism of this process and provided evidence for a novel role of silver in the catalytic cycle of the reaction, which involves silver-based complexation and activation of siloxy alkyne toward the subsequent 1,4-addition.
Related Papers
- → Hydrotris(3-mesitylpyrazolyl)borato-copper(i) alkyne complexes: synthesis, structural characterization and rationalization of their activities as alkyne cyclopropenation catalysts(2012)25 cited
- → Bimetallic Mechanism for Alkyne Cyclotrimerization with a Two-Coordinate Fe Precatalyst(2020)18 cited
- → Strong coordination of cycloheptynes by gold(i) chloride: synthesis and structure of two complexes of the type [(alkyne)AuCl](1998)58 cited
- → Reactions of Ru(CO)ClH(C5H5N)(PPh3)2 with 1-alkynes(1990)19 cited
- → Protection for the Alkyne CH(2014)2 cited