Catalytic Reductive Coupling Reactions - Michigan State University

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H-D Cross-Over ExperimentsHydrometallativeIntermediateOxidative CyclizationIntermediateXEtPh Rh(COD) 2 OTfrac-BINAPDCE, 25 o C, 2-3 hrD 2XAPhD5 mol% Catalyst LoadingX = NTs, 52% Yield(42% Alkyne Reduction)X = O, 60% YieldPhRh III LnDX Rh III LnCH 3 BCH 3H100 mol% Catalyst LoadingX = NTs, 45% Yield(8% Alkyne Reduction)X = O, 71% YieldTsNPhHCH 3CycloisomerizationWithout DeuteriumIncorporationTsNPhRh(COD) 2 OTfrac-BINAPDCE, 25 o C, 2-3 hrH 2 and D 2or DHTsNPhHHTsNPhDTsNHDPhDTsN1 2 3 4H 2 /D 2 , 95% Yield1 : 2 : 3 & 480.1 : 19.5 : 0.4PhDH, 88% Yield1 : 2 : 3 & 43.0 : 0.5 : 96.5HDJang, H.; Hughes, F.; Gong, H.; Zhang, J.; Brodbelt, J.; Krische, M. J. Am. Chem. Soc. 2005, 127, 6174—6175.
Oxidative Cyclization with Heterolytic H2 ActivationTsNTsN12PhPhPhHHDDTsNLnRh (I) XD 2-DXPhLnRh (I) DTsNRh (III) LnDPhTsNPhH 2 /D 2 , 95% Yield1 : 2 : 3 & 480.1 : 19.5 : 0.4DH, 88% Yield1 : 2 : 3 & 43.0 : 0.5 : 96.5Rh (III) LnDTsN3PhDHPhTsNPhRh (III) (D) 2 LnXDD 2TsNHDTsNDD4
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: Oxidative Cyclization Catalytic Mec
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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