Steric-Hindrance Triggered Remote Lithiations of Bulky Silyl-Substituted- Arenes

Bellan, Andreas B. und Knochel, Paul (2019): Steric-Hindrance Triggered Remote Lithiations of Bulky Silyl-Substituted- Arenes. In: Synthesis-Stuttgart, Vol. 51, No. 18: pp. 3536-3544

Abstract

Functionalized arenes bearing two bulky triethylsilyl substituents were regioselectively lithiated at the 4-position (para position) by using a mixture of nBuLi and PMDTA (N, N, N', N'', N''- pentamethyldiethylenetriamine). The resulting aryllithium species, bearing sensitive functional groups such as amides or carbamates, reacted with a range of electrophiles leading to tri- and tetrasubstituted remote-functionalized products. This lithiation could be extended to 2,2'-bis(triethylsilyl) biphenyl, for which the favored metalation site was the one where steric interference of the silyl group could be avoided.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0039-7881
• Language: English