Catalytic Reductive Coupling Reactions - Michigan State University

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1,3-Diene vs. 1,4-Diene FormationEEEREEERR'R'RR'REEH aPd (+4)αβRR'EEβ−H eliminationPd (+4)H aRR'EEL 2 PdX 2Pd (+4) ELXXLH aRR'R'H bEpath aR' and/or R = Hpath bR' or R = HPd (+4)H aRR'Pd (+4)H bH bEEEEH aRH bH bR'EEEETrost, B.; Lautens, M. J. Am. Chem. Soc. 1985, 107, 1781—1783.H aRR'H aRR'
Pd-Catalyzed CycloisomerizationsnRnRR'(+2)PdR'H bnH aRR'H aH bn(+4)PdHanor(+4)PdHbn(+2)PdRRH bR'H aRR'R'(+4)PdnH aRR'H bTrost, B.; Lautens, M.; Chan, D.; Jebaratnam, D.; Muller, T. J. Am. Chem. Soc. 1994, 116, 4255—4267.
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: Catalytic Reductive Cyclizationenyn
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 and 50: Reductive Cyclization of DiynesXR 1
Page 51 and 52: Oxidative Cyclization Catalytic Mec
Page 53 and 54: Oxidative Cyclization with Heteroly
Page 55 and 56: Hydrogen-Mediated C-C Bond Formatio
Page 57: Acknowledgments• Dr. Baker• Dr.

Catalytic Reductive Coupling Reactions - Michigan State University

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