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Lecture: Palladium-Catalyzed Complexity Generating Reactions Outline Organo-transition Metal Chemistry Transition metal-catalyzed Reaction Mechanisms Heck Reaction Heck Cascade Stille/Suzuki Coupling Reaction Allylic Alkylation Reaction Reference Mitchell. T.N. Synthesis, 1992, 803 Stille. J. K. ACIEE. 1986, 25, 508 Pure and applied chemistry 1994, 66, 213 Tetrahedron-Asymmetry 1992, 3, 1089 Organo-transition Metal Chemistry Electron Counting Ligand Exchange Oxidative Addition/Reductive Elimination Migratory Insertion/De-insertion Carbometallation/?-elimination Heck Reaction Tandem Heck Reaction Stable Neopentyl Organo-Pd-intermediate Stable Organo-Pd Intermediates Chemistry of Stable Organo-Pd Intermediate An Opportunity for Diversification Stille Coupling Reaction Suzuki Coupling Reaction Catalytic Cycle of Stille/Suzuki Coupling Tandem Heck-Stille Reaction Sequential Tandem Heck-Suzuki Reaction Termination with Carbonylation Heck-Carbonylation and Intramolecular Nucleophilic Addition Pd-catalyzed Allylic Alkylation Catalytic Cycle of Pd-catalyzed Allylic Alkylation Tandem Heck-AA Sequential Tandem AA-Heck Reaction General reactivty of substrate ; Halide, Carbonate Acetate epoxide Nucleophile : C-nucleophile- malonate, active methylene nucleophile : Heteroatom N, O, S, P, Si -based nucleophile : Hydride B-H, Sn-H, Al-H and formates : Organometallics Zn-R, Zr-R, Sn-R etc. Soft Nucleophile pKa 25 is known to attack ligand directly Active cationic form of ?3- allyl Pd complex intermediate is favored by bidentate phosphine ligand 更多资源 Chemistry involves intermediates containing transition-metal carbon bonds Formal neutral ligand L : PR3, NR3, CO, alkyne, Alkene Formal anionic ligand X : R, Ar, H, X, CN, RCO ML4 Pd 0 d10 10 e PPh3 2 e X 4 8 e 18 e ML2 Pd 0 d10 10 e PPh3 2 e X 2 4 e 14 e ML2X2 Pd II d8 8 e Ar, I 2 e, 2 e 4 e PPh3 2 e X 2 4 e 16 e Ligand Association and Ligand Dissociation Ligand dissociation is usually the
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