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Synthesis 2019; 51(18): 3536-3544
DOI: 10.1055/s-0037-1611480
DOI: 10.1055/s-0037-1611480
paper
Steric-Hindrance Triggered Remote Lithiations of Bulky Silyl-Substituted Arenes
We thank the Deutsche Forschungsgemeinschaft (DFG) for financial support. We thank Albemarle (Frankfurt, Germany) for the generous gift of chemicals.Further Information
Publication History
Received: 14 March 2019
Accepted: 19 March 2019
Publication Date:
12 June 2019 (online)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611480.
- Supporting Information
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