Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 46, Pages 20596-20603Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202008866
Keywords
catalysis; cross-coupling reactions; organolithium; phosphine ligands; ylides
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Funding
- European Research Council (ERC) under the European Union [677749]
- RESOLV - Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) under Germany's Excellence Strategy [EXC-2033, 390677874]
- UMICORE AG Co. KG
- Projekt DEAL
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Organolithium compounds are amongst the most important organometallic reagents and frequently used in difficult metallation reactions. However, their direct use in the formation of C-C bonds is less established. Although remarkable advances in the coupling of aryllithium compounds have been achieved, Csp(2)-Csp(3)coupling reactions are very limited. Herein, we report the first general protocol for the coupling or aryl chlorides with alkyllithium reagents. Palladium catalysts based on ylide-substituted phosphines (YPhos) were found to be excellently suited for this transformation giving high selectivities at room temperature with a variety of aryl chlorides without the need for an additional transmetallation reagent. This is demonstrated in gram-scale synthesis including building blocks for materials chemistry and pharmaceutical industry. Furthermore, the direct coupling of aryllithiums as well as Grignard reagents with aryl chlorides was also easily accomplished at room temperature.
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