SCREENING OF N,N-BIDENTATE PYRIDINE-BASED LIGANDS IN COPPER AND PALLADIUM CATALYSED REACTIONS MAURIZIO SOLINAS
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1 SCREEIG OF,-BIDETATE PYRIDIE-BASED LIGADS I COPPER AD PALLADIUM CATALYSED REACTIOS MAURIZIO SOLIAS
2 ITRO: Green Chemistry Principle #9 Catalytic reagents (as selective as possible) are superior to stoichiometric reagents. "CAT" CAT is a substance that changes the velocity of a reaction without itself being changed in the process. It can be used in small amounts and be recycled indefinitely (at lest in principle) Doesn t generate any waste. Catalysis is nowadays wide applied in petrochemical industry, in the pharmaceutical and fine chemical industries. All types of catalysis are generally applied in modern chemistry: heterogeneous, homogeneous, organocatalysts and, ature s own exquisite catalysts: enzymes.
3 OMOGEEOUS REACTIOS: In homogeneous catalysis the reactants, products and catalyst are all in the same phase. Often the reactants, products and catalyst are all dissolved in the same solvent. A narrower definition has become fashionable according to which homogeneous catalysis involves (organo)metallic complexes as the catalyst. ot every homogenous catalytic process contains an organometallic metal complexes : - acid and base catalysis (ester hydrolysis), - Lewis acids as catalysts (Diels-Alder reactions), - organic catalysts (thiazolium ions in Cannizzarro reactions), - porphyrin complexes (epoxidations, hydroxylations), - enzymatic processes, - co-ordination complexes (polyester condensations). Ligand effects are extremely important in homogeneous catalysis by metal complexes. One metal can give a variety of products from one single substrate simply by changing the ligands around the metal centre. Chemoselectivity Regioselectivity - Diastereoselectivity Enantioselectivity
4 The ligands 1/
5 The ligands 2/
6 Enantioselective Copper(II)-Catalyzed enry Reaction Ligand Conversion, % B-Yield, % C-Yield, % e.e., % conf S S R S R R R S S 5 (0 C) R 5 (-30 C) R 5(-30 C, 48h) R M. Solinas, B. Sechi, S. Baldino, G. Chelucci, J. Mol. Catal. A: Chemical 378 (2013)
7 Enantioselective Copper(II)-Catalyzed enry Reaction Ligand Conversion, % B-Yield, % C-Yield, % e.e., % conf S S R S R R R S S 5 (0 C) R 5 (-30 C) R 5(-30 C, 48h) R R M. Solinas, B. Sechi, S. Baldino, G. Chelucci, J. Mol. Catal. A: Chemical 378 (2013)
8 Palladium-catalysed asymmetric allylic alkylation Ligand Time, h Conversion, % Yield, % e.e., % conf S S S R R S S R S S R S M. Solinas, B. Sechi, G. Chelucci, S. Baldino, J. R. Pedro, G. Blay, J. Mol. Catal. A: Chemical 385 (2014) 73 77
9 Palladium-catalysed asymmetric allylic alkylation Ligand Time, h Conversion, % Yield, % e.e., % conf S S S R R S S R S S R S M. Solinas, B. Sechi, G. Chelucci, S. Baldino, J. R. Pedro, G. Blay, J. Mol. Catal. A: Chemical 385 (2014) 73 77
10 Cu(I)-catalysed asymmetric allylic oxidation Ligand Time, h n Yield, % e.e., % conf R R R S S S S S S S M. Solinas, B. Sechi, G. Chelucci Appl. Organometal. Chem. 2014, 28,
11 Cu(I)-catalysed asymmetric allylic oxidation Ligand Time, h n Yield, % e.e., % conf R R R S S S S S S S O O S S 21 O O S S M. Solinas, B. Sechi, G. Chelucci Appl. Organometal. Chem. 2014, 28,
12 Conclusions 1) For the enantioselective copper(ii)-catalyzed enry reaction ligand 5 gave the 1-(2-Methoxyphenyl)-2-nitroethanol in moderate yields and good enantioselectivities (up to 82% ee) under straightforward experimental conditions without the need for air or moisture exclusion. 2) For the enantioselective palladium catalyzed allylic substitution of 1,3- diphenylprop-2-enyl acetate with dimethyl malonate, the product dimethyl 1,3- diphenylprop-2-enylmalonate was produced in good yields and moderate enantioselectivities (up to 62% ee) by using ligand 13. 3) In the catalytic allylic oxidation of cyclic olefins the best yields (up to 70%) and enantioselectivities (up to 53% enantiomeric excess) were obtained with an iminopyridine based on camphane and quinoline skeletons (14).
13 Acknowledgements Giorgio Chelucci Barbara Sechi Salvatore Baldino José R. Pedro Gonzalo Blay Financial support : CR University of Sassari Regione Sardegna Fondazione Banco di Sardegna
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