Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 40, Pages 11857-11860Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201504993
Keywords
cross-coupling; ligand design; ligand effects; palladium; phosphine ligands
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Funding
- Alexander von Humboldt Foundation (Feodor Lynen Return Fellowship)
- DFG [IRTG 2027]
- FCI (Liebig Fellowship)
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A variety of chemical transformations benefit from the use of strong electron-donating ancillary ligands, such as alkylphosphines or N-heterocyclic carbenes when electron-rich metal centers are required. Herein, we describe a facile and highly modular access to monodentate and bidentate imidazolin-2-ylidenamino-substituted phosphines. Evaluation of the phosphine's electronic properties substantiate that the formal replacement of alkyl or aryl groups by imidazolin-2-ylidenamino groups dramatically enhance their donor ability beyond that of alkylphosphines and even N-heterocyclic carbenes. The new phosphines have been coordinated onto palladium(II) centers, and the beneficial effect of the novel substitution patterns has been explored by using the corresponding complexes in the palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of non-activated aryl chloride substrates.
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