Organic and Organometallic Chemistry
- Position:
Distinguished University Professor
- Address:
Department of Chemistry
University of Ottawa
10 Marie Curie
Ottawa, Ontario
K1N 6N5 Canada
- Office: D'Iorio 402
- Phone: (613)
562-5189
- Fax: (613)
562-5871
- E-Mail: howard.alper@uottawa.ca
- For Additional
details see www.nserc.ca (G.Herzberg Gold Medal in Science and Engineering),
and www.stic-csti.ca (Chair,
Government of Canada’s
Science, Technology, and Innovation Council)
|
Specific Topics:
Development of metal catalyzed
homogeneous, phase transfer, and heterogeneous mediated oxidation, reduction,
carbonylation and cyclization
reactions. These processes are being applied to the synthesis of compounds of
value to the petrochemical and/or pharmaceutical industries. Ionic liquids
are useful solvents, and sometimes promoters, for some of these reactions.
For example, the asymmetric synthesis of -lactams
by rhodium (I) catalysts is a remarkable example of a regio,
stereo, and enantiospecific reaction. Ring
expansion-carbonylation reactions have considerable
scope in terms of heteroatom and ring size. Novel palladium catalyzed, stereospecific cycloaddition
reactions of heterocumulenes (e.g. carbodiimides, isocyanates) and
aziridines or azetidines
leads to 5- and 6-membered ring heterocycles
difficult or impossible to synthesize by other means. Using chiral ligands results in the
formation of products in 88-99 %ee. Recently, dendrimer-metal complexes, anchored to silica, have been
found to be excellent, recyclable catalysts for the hydroformylation
of olefins. The length of the spacer group in the dendrimer
has a significant impact on the activity and recyclability
of the dendrimer metal complex. Finally, dendronized and non-dendronized
magnetic nanoparticle metal complexes are excellent
catalysts for highly regioselective reactions
Recent Publications:
- M.Vasylyev
and H.Alper, A New Diasteroselective
Synthesis of Hexahydro[2,1-b]oxazoles via Rhodium-catalyzed Hydroformylation-Silica-Promoted
Deformylation Sequence, Angew.Chem.Int.Ed.,
2009, 48, 1287
- H.Cao,
L.McNamee and H.Alper,
Synthesis of Substituted 3-Methyleneisoindolin-1-ones by a
Palladium-Catalyzed Sonogashira Coupling-Carbonylation-Hydroamination Sequence in Phosphonium Salt Ionic Liquids, Org.Lett.
2008, 10, 5281.
- Q.Yang,
A.Robertson and H.Alper,
Efficient Palladium/1,10-Phenanthroline
Catalyzed Reductive Carbonylation of Mono- and
Dinitroarenes to Urethanes in Phosphonium Salt Ionic Liquids, Org. Lett. 2008, 10, 5079.
- Z.Zheng
and H.Alper, Palladium-Catalyzed Carbonylation-Decarboxylation of Diethyl(2-Iodoaryl)malonates with Imidoyl
Chlorides. An Efficient
Route to Substituted
Isoquinolin-1(2H)-ones, Org.Lett. 2008, 10,
4903.
- T.Vieira,
L>Meaney, Y.L. Shi and H.Alper,
Tandem Palladium-Catalyzed N,C-Coupling/Carbonylation Sequence for the Synthesis of
2-Carboxyindoles, Org.Lett. 2008, 10, 4899.
- G.Chouhan
and H.Alper, Palladium-Catalyzed Carboxamidation Reaction and Aldol
Condensation Reaction Cascade:A
facile Approach to Ring-Fused Isoquinolinones,
Org. Lett. 2008, 10, 4987.
- S.M.Lu
and H.Alper, Sequence of Intramolecular
Carbonylation and Asymmetric Hydrogenation
Reactions: Highly Regio- and Enantioselective Synthesis of Medium Ring Tricyclic Lactams, J.Am.Chem.Soc. 2008, 130, 6451
- M.Vasylyev
and H.Alper, Synthesis of Morpholin-2-oned by Chemoselective Intramolecular
Rhodium-Catalyzed Reductive Ring Expansion of Oxazolidines,
Org. Lett. 2008, 10, 1357.
- R.Abu-Reziq,
D.Wang, M.Post and H.Alper, Separable Catalysts in One-pot Syntheses
for Green Chemistry, Chem. Mater. 2008, 20, 2544.
- T. Vieira and H.Alper, An Efficient Three-Component One-pot
Approach to the Synthesis of 2,3,4,5-Tetrahydro-1H-2-benzazepines by
Means of Rhodium-Catalyzed Hydroaminomethylation,
Org.Lett. 2008, 10, 485.
|
