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Structure-activity relationships for group 4 biaryl amidate complexes in catalytic hydroamination/cyclization of aminoalkenes
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Gott, Andrew L., Clarke, Adam J., Clarkson, Guy J. and Scott, Peter (2007) Structure-activity relationships for group 4 biaryl amidate complexes in catalytic hydroamination/cyclization of aminoalkenes. Organometallics, Vol.26 (No.7). pp. 1729-1737. doi:10.1021/om061087l ISSN 0276-7333.
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Official URL: http://dx.doi.org/10.1021/om061087l
Abstract
Synthesis of bis(carboxamide) proligands derived from (R,S)-2,2'-diamino-6,6'dimethylbiphenyl was readily achieved by treatment of the amine with acid chlorides. Direct reaction with homoleptic alkyls of the group 4 metals cleanly yielded amidate complexes. These complexes were shown by single-crystal X-ray diffraction to be monomeric in the case of titanium and dimeric in the case of zirconium. The complexes formed do not yield well-defined cations upon reaction with standard borate/borane activators, and although some hydroamination catalysis was observed, it was not at a rate that is useful. In-situ treatment of Zr(NMe2)(4) with the proligands H2L1-4 yielded complexes of varying nuclearity depending on the steric bulk of the amide substituents, but in contrast to the metal alkyl series, mononuclear species are accessible; the mesityl derivative [(S)-(LZr)-Zr-4(NMe2)(2)] was found to be a highly enantioselective catalyst for the hydroamination/cyclization of 1-amino-2,2-dimethylpent-4-ene, with an enantiomeric excess of 91%.
| Item Type: | Journal Article | ||||
|---|---|---|---|---|---|
| Subjects: | Q Science > QD Chemistry | ||||
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
| Journal or Publication Title: | Organometallics | ||||
| Publisher: | American Chemical Society | ||||
| ISSN: | 0276-7333 | ||||
| Official Date: | 26 March 2007 | ||||
| Dates: |
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| Volume: | Vol.26 | ||||
| Number: | No.7 | ||||
| Number of Pages: | 9 | ||||
| Page Range: | pp. 1729-1737 | ||||
| DOI: | 10.1021/om061087l | ||||
| Status: | Peer Reviewed | ||||
| Publication Status: | Published | ||||
| Access rights to Published version: | Restricted or Subscription Access |
Data sourced from Thomson Reuters' Web of Knowledge
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