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

A Pd­(OAc)2/P­(OPh)3 combination catalyzed Tsuji–Trost-type allylic amination under aerobic conditions. Both aromatic and aliphatic secondary amines were transformed into the corresponding allylic amines with a tiny amount of the catalyst system (typically 0.02 mol % Pd), only when allylic phosphate...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-03, Vol.87 (5), p.2864-2872
Main Authors: Yurino, Taiga, Saito, Sunaho, Ichihashi, Mizuki, Ohkuma, Takeshi
Format: Article
Language:English
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Summary:A Pd­(OAc)2/P­(OPh)3 combination catalyzed Tsuji–Trost-type allylic amination under aerobic conditions. Both aromatic and aliphatic secondary amines were transformed into the corresponding allylic amines with a tiny amount of the catalyst system (typically 0.02 mol % Pd), only when allylic phosphates were employed as electrophiles. Other typical electrophiles, such as allylic acetate and carbonate, were marginally reactive. A Pd(0) complex, Pd­[P­(OPh)3]3, formed in situ was suggested as an active species by mechanistic experiments.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02768