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Aerobic Allylic Amination Catalyzed by a Pd(OAc)2/P(OPh)3 System with Low Catalyst Loading

Taiga Yurino*, Sunaho Saito, Mizuki Ichihashi and Takeshi Ohkuma*

*Faculty of Engineering, Hokkaido University, Kita 13, Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan, Email: tyurinoeng.hokudai.ac.jp, ohkumaeng.hokudai.ac.jp

T. Yurino, S. Saito, M. Ichihashi, T. Ohkuma, J. Org. Chem., 2022, 87, 2864-2872.

DOI: 10.1021/acs.joc.1c02768

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Abstract

The combination of Pd(OAc)2/P(OPh)3 catalyzed Tsuji-Trost-type allylic aminations under aerobic conditions at very low catalyst loadings. Both aromatic and aliphatic secondary amines were transformed into the corresponding allylic amines in the presence of allylic phosphates as electrophiles. Other electrophiles, such as allylic acetate and carbonate, were marginally reactive.

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proposed mechanism

Key Words

Tsuji-Trost reaction, allylic amination

ID: J42-Y2022