Catalytic Reductive Coupling Reactions - Michigan State University

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Oxidative Cyclization with Homolytic H2 ActivationTsNTsN12PhPhPhHHDDTsNPhLnRh (I) XTsNRh (III) LnXPhTsNPhH 2 /D 2 , 95% Yield1 : 2 : 3 & 480.1 : 19.5 : 0.4DH, 88% Yield1 : 2 : 3 & 43.0 : 0.5 : 96.5Rh (III) LnXTsN3PhDHPhTsNPhRh (III) DLnXDD 2TsNHDTsNDD4
Hydrogen-Mediated C-C Bond FormationHomolytic activation of H 2HH MLnH HHC-H reductiveXR 1 MLn eliminationR 1 HR 2 X R 2R 1 LnM XH 2 (1atm)R 2 M X (cat)Heterolytic activation of H 2H XHXR 1 MLnR 1H MLnR 2 R 2(H-X, base)H R 3 H 2ConventionalreductionMLnR 3XR 1 LnM XH R 3 R 3R 2MLnR 1R 2Homolytic activation of H 2H 2H MLnR 1 HR 2 XHR 3C-C bondformationMLnJang, H.; Krische, M. Acc. Chem. Res. 2004, 37, 653—661.
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 and 50: Reductive Cyclization of DiynesXR 1
Page 51 and 52: Oxidative Cyclization Catalytic Mec
Page 53: Oxidative Cyclization with Heteroly
Page 57: Acknowledgments• Dr. Baker• Dr.
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Catalytic Reductive Coupling Reactions - Michigan State University

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