Catalytic Reductive Coupling Reactions - Michigan State University

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Pd(0)-Catalyzed Allylic AlkylationsEEOAcEE(Ph 3 P) 4 Pd (3-5 mol%)NaH, THF, reflux85%EEEENu Pd(PPh 3 ) 4OAcEETrost-Tsuji ReactionLPdLNuLPdLOAcEOAcNuLPd LTrost, B. Acc. Chem. Res. 1980, 13, 385—393.
Pd(0)-Catalyzed <strong>Coupling</strong>sallyl acetateEE(Ph 3 P) 4 Pd (3-5 mol%)NaH, THF, refluxentry allyl acetate enyne yield1EEenyne85%OAcEE2OAcEE87%EE3OAc87%OAcE4E71%Trost, B.; Lautens, M. J. Am. Chem. Soc. 1985, 107, 1781—1783.
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: Alder-Ene ReactionHXYH Y XHYXHYXX Y
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 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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