Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 47, Pages 25151-25160Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202110450
Keywords
allyl ligands; C-C coupling; cross coupling; homogeneous catalysis; palladium
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Funding
- Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) under Germany's Excellence [EXC-2033-390677874-RESOLV, SFB TRR88]
- BMBF
- state of NRW (Center of Solvation Science ZEMOS)
- Fonds der chemischen Industrie FCI
- CSC
- Projekt DEAL
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Halogen-bridged methylnaphthyl (MeNAP) palladium dimers, presented as versatile Pd precursors, demonstrate excellent catalytic performance by in situ conversion into well-defined monoligated complexes. They show benchmark activities in challenging reactions, enable record-setting yields, and can achieve previously elusive cross-couplings.
Halogen-bridged methylnaphthyl (MeNAP) palladium dimers are presented as multipurpose Pd-precursors, ideally suited for catalytic method development and preparative organic synthesis. By simply mixing with phosphine or carbene ligands, they are in situ converted into well-defined monoligated complexes. Their catalytic performance was benchmarked against state-of-the-art systems in challenging Buchwald-Hartwig, Heck, Suzuki and Negishi couplings, and ketone arylations. Their use enabled record-setting activities, beyond those achievable by optimization of the ligand alone. The MeNAP catalysts permit syntheses of tetra-ortho-substituted arenes and bulky anilines in near-quantitative yields at room temperature, allow mono-arylations of small ketones, and enable so far elusive cross-couplings of secondary alkyl boronic acids with aryl chlorides.
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