Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 20, Pages 7721-7725Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202001326
Keywords
chemoselectivity; cross-coupling; DFT calculations; homogeneous catalysis; palladium
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Funding
- Alexander von Humboldt-Stiftung Funding Source: Medline
- H2020 European Research Council [ERC-637993] Funding Source: Medline
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Contrary to the general belief that Pd-catalyzed cross-coupling at sites of severe steric hindrance are disfavored, we herein show that the oxidative addition to C-Br ortho to an adamantyl group is as favored as the corresponding adamantyl-free system due to attractive dispersion forces. This enabled the development of a fully selective arylation and alkylation of C-Br ortho to an adamantyl group, even if challenged with competing non-hindered C-OTf or C-Cl sites. The method makes use of an air-stable Pd-I dimer and enables straightforward access to diversely substituted therapeutically important adamantylarenes in 5-30 min.
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