Broadening the scope of group 4 hydroamination catalysis using a tethered ureate ligand

David C. Leitch, Philippa R. Payne, Christine R Dunbar, Laurel L. Schafer

Research output: Contribution to journalArticlepeer-review

138 Scopus citations

Abstract

(Chemical Equation Presented) A broadly applicable group-4-based precatalyst for the hydroamination of primary and secondary amines was developed. Screening experiments involving a series of amide and urea proligands led to the discovery of a tethered bis(ureate) zirconium complex with unprecedented reactivity in the intermolecular hydroamination of alkynes and the intramolecular hydroamination of alkenes. This catalyst system is effective with primary and secondary amines, 1,2-disubstituted alkenes, and heteroatom-containing functional groups, including ethers, silanes, amines, and heteroaromatics. The gem-disubstituent effect is not required for cyclization. The catalyst is generally regioselective for the anti-Markovnikov product of intermolecular alkyne hydroamination, and chemoselective for hydroamination over C-alkylation when forming 6- and 7-membered rings from aminoalkenes.

Original languageEnglish (US)
Pages (from-to)18246-18247
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number51
DOIs
StatePublished - Dec 30 2009

Fingerprint Dive into the research topics of 'Broadening the scope of group 4 hydroamination catalysis using a tethered ureate ligand'. Together they form a unique fingerprint.

Cite this