Silylarene Hydrogenation: A Strategic Approach that Enables Direct Access to Versatile Silylated Saturated Carbo‐ and Heterocycles | Zendy

Wiesenfeldt Mario P. | Zendy; Knecht Tobias | Zendy; Schlepphorst Christoph | Zendy; Glorius Frank | Zendy

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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 ).

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