Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 696, Issue 1, Pages 2-6Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2010.08.039
Keywords
Zirconium; Cyclam; Hydroamination; Nitrogen heterocycles; Aminoalkenes; Intramolecular cyclization
Categories
Funding
- Fundacao para a Ciencia e a Tecnologia, Portugal [PTDC/QUI/66187/2006, SFRH/BPD/26745/2006, SFRH/BD/29986/2006, SFRH/BD/44295/2008]
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The syntheses of (Bn(2)Cyclam)Zr(NMe2)(2) (1), (Bn(2)Cyclam)Zr(NH2,6-MePh)Cl (2) and (Bn(2)Cyclam)Zr(N2,6-MePh) (3) are described. The reactivity of 1, 3, (Bn(2)Cyclam)Zr(CH2Ph)(2) (4) and ((C6H4CH2)(2)Cyclam)Zr (5) as hydroamination catalysts of aminoalkenes is reported. High conversions of the primary gem-disubstituted aminoalkenes in 5- or 6-member ring N-heterocycles were observed. Reactions of 1, 4 and 5 with CH2 = CHCH2CPh2CH2NH2 gave (Bn(2)Cyclam)Zr(NHR)(2) (6) (R = CH2CPh2CH2CH = CH2) that on heating converts sequentially into the mono-ortho-metallated species ((C6H4CH2)BnCyclam)Zr(NHR) (7) and the bis-ortho-metallated ((C6H4CH2)(2)Cyclam)Zr (5), simultaneously with the hydroamination product. (C) 2010 Elsevier B.V. All rights reserved.
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