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Silylarene Hydrogenation: A Strategic Approach that Enables Direct Access to Versatile Silylated Saturated Carbo‐ and Heterocycles
Author(s) -
Wiesenfeldt Mario P.,
Knecht Tobias,
Schlepphorst Christoph,
Glorius Frank
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201804124
Subject(s) - silylation , chemistry , yield (engineering) , alkoxy group , organic chemistry , scope (computer science) , catalysis , combinatorial chemistry , materials science , computer science , alkyl , metallurgy , programming language
We report a method to convert readily available silylated arenes into silylated saturated carbo‐ and heterocycles by arene hydrogenation. The scope includes alkoxy‐ and halosilyl substituents. Silyl groups can be derivatized into a plethora of functionalities and find application in organic synthesis, materials science, and pharmaceutical, agrochemical, and fragrance research. However, silylated saturated (hetero‐ ) cycles are difficult to access with current technologies. The yield of the hydrogenation depends on the amount of the silica gel additive. This silica effect also enables a significant improvement of a previously disclosed method for the hydrogenation of highly fluorinated arenes (e.g., to all‐ cis ‐C 6 H 6 F 6 ).