Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 47, Pages 14793-14797Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201608535
Keywords
alkyl bromides; C-C coupling; homogeneous catalysis; palladium; remote functionalization
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Funding
- Agence National de la Recherche [ANR-14-CE06-0001]
- China Scholarship Council
- Swiss National Science Foundation [200021_165987]
- University of Basel
- Agence Nationale de la Recherche (ANR) [ANR-14-CE06-0001] Funding Source: Agence Nationale de la Recherche (ANR)
- Swiss National Science Foundation (SNF) [200021_165987] Funding Source: Swiss National Science Foundation (SNF)
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Hydrocarbons are still the most important precursors of functionalized organic molecules, which has stirred interest in the discovery of new C-H bond functionalization methods. We describe herein a new step-economical approach that enables C-C bonds to be constructed at the terminal position of linear alkanes. First, we show that secondary alkyl bromides can undergo in situ conversion into alkyl zinc bromides and regioconvergent Negishi coupling with aryl or alkenyl triflates. The use of a suitable phosphine ligand favoring Pd migration enabled the selective formation of the linear cross-coupling product. Subsequently, mixtures of secondary alkyl bromides were prepared from linear alkanes by standard bromination, and regioconvergent cross-coupling then provided access to the corresponding linear arylation product in only two steps.
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