Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 11, Pages 3620-3624Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201510328
Keywords
aryl lithium compounds; homocoupling; palladium; symmetric biaryls; total synthesis
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Funding
- Netherlands Organization for Scientific Research (NWO-CW) for a VICI grant
- NWO-CW, National Research School Catalysis (NRSC-Catalysis)
- European Research Council (ERC) [227897]
- Royal Netherland Academy of Arts and Sciences (KNAW)
- Ministry of Education, Culture and Science (Gravitation program) [024.601035]
- Intra-European Marie Curie Fellowship [FP7-PEOPLE-2011-IEF-300826]
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A palladium-catalyzed direct synthesis of symmetric biaryl compounds from aryl halides in the presence of tBuLi is described. Insitu lithium-halogen exchange generates the corresponding aryl lithium reagent, which undergoes a homocoupling reaction with a second molecule of the aryl halide in the presence of the palladium catalyst (1mol%). The reaction takes place at room temperature, is fast (1h), and affords the corresponding biaryl compounds in good to excellent yields. The application of the method is demonstrated in an efficient asymmetric total synthesis of mastigophoreneA. The chiral biaryl axis is constructed with an atropselectivity of 9:1 owing to catalyst-induced remote point-to-axial chirality transfer.
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