Catalytic Reductive Coupling Reactions - Michigan State University

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Rh-Catalyzed Intramolecular Alder-Ene <strong>Reactions</strong>Pdppb =1,4-Bis(diphenylphosphino)butanePOR 1 OR 2CataystAgSbF 6ClCH 2 CH 2 ClR 11 2O*OR 2PPh 2Ph 2 P(S)-BINAPentry R 1 R 2 catalyst ligand product yield (%) ee (%)1 Ph Et [Rh(COD)Cl]2 ---- 2a < 5 ----2 Ph Me [Rh(COD)Cl]2 dppb 2b 84 ----3 Ph Et [Rh(COD)Cl]2 (R)-BINAP (-)-2c 96 > 99.54 Ph OAc [Rh(COD)Cl]2 (S)-BINAP (+)-2d 96 99.75 Ph Et [Rh(COD)Cl]2 (S)-BINAP (+)-2e 93 > 996 Ph OAc [Rh(COD)Cl]2 (R)-BINAP (-)-2f 96 >99Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490—6491Lei, A.; He, M.; Wu, S.; Zhang, X. Angew. Chem. Int. Ed. 2002, 41, 3457—3460.
Mechanism via Oxidative CyclometallationRHXRXOO[Rh I ] +OOHROM HOcXRM = [Rh III ] +XMHORO[Rh I ] +aHXClOObx = alkyl, OH, OAc, OBz, HOOTong, X.; Li, D.; Zhang, Z.; Zhang, X. J. Am. Chem. Soc. 2004, 126, 7601—7607.
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: Outline• Discovery and Developmen
Page 33 and 34: Mechanism via Oxidative Cyclometall
Page 35 and 36: Reaction Mechanism via π-Allyl Rho
Page 37 and 38: Outline• Discovery and Developmen
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.

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