N-Protonated Acridinium Catalyst Enables Anti-Markovnikov Hydration of Unconjugated Tri- and Disubstituted Olefins DOI Creative Commons

Boris A. van der Worp,

Tobias Ritter

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: 147(6), P. 4736 - 4742

Published: Jan. 31, 2025

The preparation of alcohols with anti-Markovnikov selectivity directly from olefins and water is a sought-after reaction due to its atom-economy potential cost-effectiveness. Herein, we present the first general method for direct, catalytic hydration unconjugated tri- disubstituted olefins. key advancement made possible by an oxidative (E*red = 2.15 V) N-H acridinium catalyst, which allowed functionalization alkenes that were previously unreactive in such transformations their high oxidation potential. developed protocol not limited but also enables other hydrofunctionalizations, as hydroetherifications, following same mechanistic pathway.

Language: Английский

N-Protonated Acridinium Catalyst Enables Anti-Markovnikov Hydration of Unconjugated Tri- and Disubstituted Olefins DOI Creative Commons

Boris A. van der Worp,

Tobias Ritter

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: 147(6), P. 4736 - 4742

Published: Jan. 31, 2025

The preparation of alcohols with anti-Markovnikov selectivity directly from olefins and water is a sought-after reaction due to its atom-economy potential cost-effectiveness. Herein, we present the first general method for direct, catalytic hydration unconjugated tri- disubstituted olefins. key advancement made possible by an oxidative (E*red = 2.15 V) N-H acridinium catalyst, which allowed functionalization alkenes that were previously unreactive in such transformations their high oxidation potential. developed protocol not limited but also enables other hydrofunctionalizations, as hydroetherifications, following same mechanistic pathway.

Language: Английский

Citations

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