Journal
ORGANOMETALLICS
Volume 32, Issue 7, Pages 2210-2215Publisher
AMER CHEMICAL SOC
DOI: 10.1021/om4000743
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Funding
- MEXT [24109010]
- JSPS [24.3950]
- MEXT program Elements Strategy Initiative to Form Core Research Center
- Grants-in-Aid for Scientific Research [24109010] Funding Source: KAKEN
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The iridium(I) complex [IrCl(BPEP-H)] (1), coordinated with 2,6-bis[2-(2,4,6-tri-tert-butylphenyl)-2-phosphaethenyl]pyridine (BPEP-H) as a PNP-pincer-type phosphaalkene ligand, has been synthesized and fully characterized by elemental analysis, NMR spectroscopy, and X-ray diffraction analysis. Complex 1 (1 mol %) catalyzes N-alkylation of primary and secondary amines with alcohols, leading to the selective formation of secondary and tertiary amines, respectively. Primary amines are smoothly alkylated with a variety of benzylic and aliphatic alcohols (1 or 3 equiv) at 100 degrees C under basic conditions (CsOH, 10 mol %) to give the corresponding secondary amines in good to high yields. On the other hand, N-alkylation of secondary amines with benzyl alcohol (3 equiv) proceeds in the presence of KH2PO4 (5 mol %) at 140 degrees C to afford tertiary amines in high yields.
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