Catalytic Reductive Coupling Reactions - Michigan State University

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Hydrometallative <strong>Catalytic</strong> MechanismRegio-Determining C-D Bond Formation Precedes C-C Bond FormationPhEEPhPhEEDRh (I) LnPhPhRh (I) Ln OTfD 2Rh (I) Ln D-DOTfEEDRh (I) LnPhPhEEPhDDEEDRh (III) (D) 2 LnPhD 2PhJang, H.; Krische, M. J. Am. Chem. Soc. 2004, 126, 7875—7880.
Oxidative Cyclization <strong>Catalytic</strong> MechanismRegio-Determining C-C Bond Formation Precedes C-D Bond FormationEEPhPhEEPhRh (III) LnDPhRh (I) Ln OTfD 2Rh (I) Ln D-DOTfEEPhRh (I) LnDPhEEPhDDPhEEPhPhRh (III) (D) 2 LnD 2Jang, H.; Krische, M. J. Am. Chem. Soc. 2004, 126, 7875—7880.
Page 1 and 2: Catalytic ReductiveCoupling Reactio
Page 3 and 4: Reductive HydrogenationClPh 3 PRhPP
Page 5 and 6: Outline• Discovery and Developmen
Page 7 and 8: Alder-Ene ReactionHXYH Y XHYXHYXX Y
Page 9 and 10: Pd(0)-Catalyzed Couplingsallyl acet
Page 11 and 12: Discovery of Reductive CyclizationE
Page 13 and 14: Screening Pd(2+) CatalystsEEEEcatal
Page 15 and 16: Catalytic Reductive Cyclizationenyn
Page 17 and 18: Pd-Catalyzed CycloisomerizationsnRn
Page 19 and 20: Nickel Catalyzed Coupling Reactions
Page 23 and 24: Reductive Couplings of Allenes and
Page 25 and 26: Ni-Catalyzed Reductive Couplings of
Page 27 and 28: Total Synthesis of Amphidinolide T1
Page 31 and 32: Mechanism via Oxidative Cyclometall
Page 33 and 34: Mechanism via Oxidative Cyclometall
Page 35 and 36: Reaction Mechanism via π-Allyl Rho
Page 39 and 40: Intramolecular Reductive Aldolizati
Page 41 and 42: Heterolytic Hydrogen ActivationPh 3
Page 43 and 44: Proposed Catalytic MechanismOO CH 3
Page 45 and 46: Reductive Condensation ContinuedOLn
Page 47 and 48: Reductive Condensation ContinuedPre
Page 49: Reductive Cyclization of DiynesXR 1
Page 53 and 54: Oxidative Cyclization with Heteroly
Page 55 and 56: Hydrogen-Mediated C-C Bond Formatio
Page 57: Acknowledgments• Dr. Baker• Dr.

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