Catalytic Reductive Coupling Reactions - Michigan State University

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C-C Bond Formation with H2 as Terminal ReductantOAcMe1 mol% [Rh(CO) 2 acac]CO/H 2 (1:1), 80 o C80% yieldOanti78%Osyn22%AcMeAcMeOOPh 3 PPh 3 PBreit, B. Acc. Chem. Res. 2003, 36, 264—275.Evans, D.; Osborn, J.; Wilkinson, G. J. Chem. Soc. A 1968, 3133—3142.H 2ROPh 3 PHHRhRhCOHCOOHPPh 3ORHHRPh 3 PPh 3 PPh 3 PHRhCOHRhCOPPh 3PPh 3HydroformylationPh 3 PPh 3 P-PPh 3RhCORHCORPh 3 PPh 3 PPh 3 PRhCOCOHRhRHPPh 3COR
Intramolecular <strong>Reductive</strong> AldolizationPhOOHCatalyst (10 mol%)Ligand (24 mol%)H 2 (1 atm), Addditive (30 mol%)DCE, 25 o CPhOOHPhOOHentry catalyst ligand additive yield aldol (syn:anti) yield 1,4-reduction1 Rh(PPh3)3Cl --- --- 1% (99:1) 95%2 Rh(COD)2OTf PPh3 --- 21% (99:1) 25%3 Rh(COD)2OTf PPh3 KOAc 59% (58:1) 21%4 Rh(COD)2OTf (p-CF3Ph)3P --- 57% (14:1) 22%5 Rh(COD)2OTf (p-CF3Ph)3P KOAc 89% (10:1) 0.1%Jang, H.; Huddleston, R.; Krische, M. J. Am. Chem. Soc. 2002, 124, 15156—15157.
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 29 and 30: Outline• Discovery and Developmen
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 37: Outline• Discovery and Developmen
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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