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Anti-Markovnikov
Hydroamination of Alkenes
Published
Papers:Senior Investigators: Prof. John Hartwig (UC-Berkeley), Prof. Karen Goldberg (U. Wash.). The discovery of efficient catalysts for the hydroamination of alkenes could have a tremendous impact on the synthesis of pharmaceuticals, of fine chemicals and of commodity chemicals. Especially desirable would be a process that allows the selective formation of the anti-Markovnikov product. The Hartwig and Goldberg laboratories are collaborating to find solutions to this challenging and as yet unsolved synthetic problem. To develop catalysts for the direct,
anti-Markovnikov hydroamination of alkenes,
elementary reactions that form C(sp3)-N
bonds from metal-akyl complexes or form the C(sp3)-N
bonds in aminoalkyl complexes are needed. These
reactions are the challenging steps of two potential
catalytic cycles for anti-Markovnikov hydroamination
shown below. Marquard, S. L.; Hartwig, J. F. “C(sp3)-O Bond-Forming Reductive Elimination of Ethers from Bisphosphine-Ligated Benzylpalladium(II) Aryloxide Complexes” Angew. Chem. Int. Ed. Eng., 2011, 50, 7119-7123. (DOI: 10.1002/anie.201101088) Marquard, S. L.; Rosenfeld, D. C.; Hartwig, J. F., "C(sp3)-N Bond-Forming Reductive Elimination of Amines: Reactions of Bisphosphine-Ligated Benzylpalladium(II) Diarylamido Complexes", Angew. Chem. Int. Ed. Eng., 2010, 49, 793-796. (DOI 10.1002/anie.200904032) |
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