Highly Regioselective Remote Lithiation of Functionalized 1,3-bis-Silylated Arenes

Bellan, Andreas B. und Knochel, Paul (2019): Highly Regioselective Remote Lithiation of Functionalized 1,3-bis-Silylated Arenes. In: Angewandte Chemie-International Edition, Vol. 58, No. 6: pp. 1838-1841

Abstract

Substituted arenes flanked by two bulky triethylsilyl groups were regiospecifically lithiated at the 5-position with nBuLiPMDTA at 25 degrees C. The resulting aryllithiums reacted with a broad range of electrophiles such as ketones, isocyanates, Weinreb amides, allyl bromides, and CO2 at 25 degrees C. These bis-silylated arenes were then converted in simple reaction sequences into silyl-free tetrasubstituted arenes. This remote lithiation was extended to 2,6-bis(triethylsilyl)pyridine as well as 3,3-bis(triethylsilyl)biphenyl.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1433-7851
• Language: English