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Pd-PEPPSI-IPentCl: A Highly Effective Catalyst for the Selective Cross-Coupling of Secondary Organozinc Reagents


  • This work was supported by NSERC (Canada) and the Ontario Research Fund (ORF, Ontario). PEPPSI=pyridine-enhanced precatalyst preparation, stabilization, and initiation; IPentCl refers to an N-heterocyclic carbene ligand.


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No migration? No problem! A series of new N-heterocyclic carbene based Pd complexes has been created and evaluated in the Negishi cross-coupling of aryl and heteroaryl chlorides, bromides, and triflates with a variety of secondary alkylzinc reagents (see scheme). The direct elimination product is nearly exclusively formed; in most examples there is no migratory insertion at all.

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