Synthesis, structure, and catalytic activity of Ti-IV and Zr-IV complexes derived from (R)-2,2 '-diamino-1,1 '-binaphthyl-based N-4-donor ligands

Reaction of (R)-bis(pyrrol-2-ylmethyleneamino)-1,1'-binaphthyl (1H(2)) or (R)-N,N'-bis(pyridin-2-ylmethyl)-1,1'-binaphthyl-2,2'-diamine (H-2(2)) with Zr(NMe2)(4) (1 equiv.) gives chiral zirconium amides 1-Zr(NMe2)(2)center dot C7H8 (4 center dot C7H8) or 2-Zr(NMe2)(2) (6) in good...

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Published inEuropean journal of inorganic chemistry Vol. 2008; no. 7; pp. 1135 - 1140
Main Authors Xiang, Li, Song, Haibin, Zi, Guofu
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.03.2008
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Physical Sciences
Science & Technology
ENANTIOSELECTIVE INTRAMOLECULAR HYDROAMINATION
titanium
ORGANOLANTHANIDES
REACTIVITY
AMINOALKENES
asymmetric catalysis
hydroamination
YTTRIUM
N ligands
INTERMOLECULAR HYDROAMINATION
ASYMMETRIC HYDROAMINATION
zirconium
EFFICIENT
AMIDATE COMPLEXES
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Summary:Reaction of (R)-bis(pyrrol-2-ylmethyleneamino)-1,1'-binaphthyl (1H(2)) or (R)-N,N'-bis(pyridin-2-ylmethyl)-1,1'-binaphthyl-2,2'-diamine (H-2(2)) with Zr(NMe2)(4) (1 equiv.) gives chiral zirconium amides 1-Zr(NMe2)(2)center dot C7H8 (4 center dot C7H8) or 2-Zr(NMe2)(2) (6) in good yields, respectively. Under similar conditions, 1H(2) reacts with Ti(NMe2)(4) (1 equiv.) to give chiral titanium amide 1-Ti(NMe2)(2)center dot C6H6 (3 center dot C6H6), whereas treatment of 2H(2) with Ti(NMe2)(4) (1 equiv.) leads to the isolation of his(ligated) product (2)(2)-Ti-C7H8 (5 center dot C7H8) in 74 % yield. All complexes were characterized by various spectroscopic techniques, elemental analysis, and X-ray diffraction analysis. Zirconium amides 4 and 6 are active catalysts for the asymmetric hydroamination/cyclization of aminoalkenes, and cyclic amines were obtained in good-to-excellent yields with moderate ee values (up to 59 %); titanium amides 2 and 5 were not active under the reaction conditions. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
ISSN:1434-1948
1099-0682
DOI:10.1002/ejic.200701105