Journal
ORGANOMETALLICS
Volume 37, Issue 19, Pages 3243-3247Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.organomet.8b00617
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Funding
- National Science Foundation Center for Enabling New Technologies through Catalysis [CHE-1205189]
- National Science Foundation [CHE-1531468]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1205189] Funding Source: National Science Foundation
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Reductive eliminations to form alkyl-nitrogen bonds are rare, and examples of this reaction from isolated complexes containing simple, unstabilized primary alkyl groups have not been observed. We report the synthesis of stable neopentylpalladium(II) anilido and methyleneamido complexes that undergo reductive elimination to form the C(sp(3))-N bonds in N-neopentyl anilines and N-neopentyl imines, respectively. The synthesis and isolation of these complexes were enabled by weak chelation of palladium by P,O ancillary ligands. DFT calculations suggest that neopentylpalladium(II) complexes undergo reductive elimination by a concerted mechanism resembling a migration of the alkyl ligand to the nitrogen either following initial dissociation of the oxygen donor or in concert with lengthening of the Pd-O bond, depending on the identities of the reacting and ancillary ligands.
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