Affiliation:
1. Department of Chemistry, Ludwig-Maximilians-Universität München
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.
Subject
Organic Chemistry,Catalysis
Cited by
5 articles.
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