Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Download PDF
Synfacts 2024; 20(01): 0033
DOI: 10.1055/s-0043-1772902
DOI: 10.1055/s-0043-1772902
Metals in Synthesis
Rhodium-Catalyzed Addition of Arylsilanes to Electrophiles by π-Coordination-Driven Desilylation
Authors
Lin Y,
Shi H.
*
Westlake University, Hangzhou, P. R. of China
Rhodium-Catalyzed Addition of (Trialkylsilyl)arenes to Electrophiles via π‑Coordination-Driven C–Si Bond Activation.
J. Am. Chem. Soc. 2023;
145: 22753-22761
DOI: 10.1021/jacs.3c08603
Rhodium-Catalyzed Addition of (Trialkylsilyl)arenes to Electrophiles via π‑Coordination-Driven C–Si Bond Activation.
J. Am. Chem. Soc. 2023;
145: 22753-22761
DOI: 10.1021/jacs.3c08603
Significance
A rhodium(III)-catalyzed desilylation of (trialkylsilyl)arenes with fluoride is reported, giving access to stabilized phenyl anion intermediates that eventually undergo addition to electrophiles. The desilylation is facilitated by the π-coordination of the rhodium complex.
Scroll to top
Comment
Mechanistic as well as computational studies support the shown mechanism, involving nucleophilic addition of the fluoride to the aromatic ring, followed by 1,2-migration and C(sp2)–Si heterolysis.
Scroll to top
Scroll to top
Publication History
Article published online:
08 December 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany