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Asymmetric hydroamination catalyzed by a new chiral zirconium system: reaction scope and mechanism.
Chem Commun (Camb)
April 2015
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China.
A new class of chiral zirconium complexes supported by chiral tridentate [O(-)NO(-)]-type of ligands derived from amino acids were synthesized and structurally characterized. They catalyzed asymmetric hydroamination/cyclization of primary aminoalkenes to give five- and six-membered N-heterocyclic amines with up to 94% ee.
View Article and Find Full Text PDFN-heterocyclic carbene (NHC) complexes of group 4 transition metals.
Chem Soc Rev
April 2015
Department of Chemistry, Fudan University, Shanghai 200433, China.
Since the discovery of a stable N-heterocyclic carbene (NHC), the use of NHCs in chemistry has developed rapidly over the past two decades. These interesting compounds are predominantly employed in organometallic chemistry as ligands for various metal centers, and as organocatalysts for a variety of transformations. In particular, the NHC transition metal complexes have received widespread attention, and significant progress has been made in the development of group 4 NHC-complexes in the last few years.
View Article and Find Full Text PDFNeutral Zr(IV) and Hf(IV) dimethyl complexes stabilized by unsymmetrical dianionic {N,C,N'} pincer ligands have been prepared from their corresponding bis-amido complexes upon treatment with AlMe₃. Their structure consists of a central ó-bonded aryl donor group (C) capable of forming robust M-C bonds with the metal center, enforced by the synergic effect of both the coordination of peripheral donor groups (N) and the chelating rigid structure of the {N,C,N} ligand framework. Such a combination translates into systems having a unique balance between stability and reactivity.
View Article and Find Full Text PDFCationic Group-IV pincer-type complexes for polymerization and hydroamination catalysis.
Dalton Trans
December 2013
Institute of Chemistry of OrganoMetallic Compounds ICCOM-CNR, Via Madonna del Piano, 10-50019, Sesto F.no., Florence, Italy.
Neutral Zr(IV) and Hf(IV) dimethyl complexes stabilized by unsymmetrical dianionic {N,C,N'} pincer ligands have been prepared from their corresponding bis-amido complexes upon treatment with AlMe3. Their structure consists of a central σ-bonded aryl donor group (C) capable of forming robust M-C bonds with the metal center, enforced by the synergic effect of both the coordination of peripheral donor groups (N) and the chelating rigid structure of the {N,C,N} ligand framework. Such a combination translates into systems having a unique balance between stability and reactivity.
View Article and Find Full Text PDFHighly enantioselective zirconium-catalyzed cyclization of aminoalkenes.
J Am Chem Soc
May 2013
Department of Chemistry and U.S. Department of Energy Ames Laboratory, Iowa State University, Ames, Iowa 50011, USA.
Aminoalkenes are catalytically cyclized in the presence of cyclopentadienylbis(oxazolinyl)borato group 4 complexes {PhB(C5H4)(Ox(R))2}M(NMe2)2 (M = Ti, Zr, Hf; Ox(R) = 4,4-dimethyl-2-oxazoline, 4S-isopropyl-5,5-dimethyl-2-oxazoline, 4S-tert-butyl-2-oxazoline) at room temperature and below, affording five-, six-, and seven-membered N-heterocyclic amines with enantiomeric excesses of >90% in many cases and up to 99%. Mechanistic investigations of this highly selective system employed synthetic tests, kinetics, and stereochemistry. Secondary aminopentene cyclizations require a primary amine (1-2 equiv vs catalyst).
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