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Synthesis 2022; 54(10): 2350-2360
DOI: 10.1055/a-1730-2540
DOI: 10.1055/a-1730-2540
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Copper-Catalyzed Allylation of Amines with Cyclopropyldiphenylsulfonium Trifluoromethanesulfonate
Authors
We thank Wuhan University of Technology and the ‘Hundred Talent’ Program of Hubei Province (China) for financial support.
Abstract
Cyclopropyldiphenylsulfonium salt, a famous ylide precursor previously extensively employed in the preparation of cyclic compounds, has been successfully utilized as an efficient allylation reagent in this work. The copper-catalyzed reactions of cyclopropyldiphenylsulfonium trifluoromethanesulfonate with amines in the presence of an appropriate ligand provided the N-allylated products in good yields. Aliphatic/aromatic amines and primary/secondary amines were all converted under mild reaction conditions. This protocol was also applicable to N-functionalization of drug molecules, supplying the corresponding N-allylated compounds in satisfactory yields. The reaction, which showed good functional group tolerance with a wide range of substrates and excellent chemoselectivity, offers an interesting method for the synthesis of N-allyl amines.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1730-2540.
- Supporting Information (PDF) (opens in new window)
Publication History
Received: 05 December 2021
Accepted after revision: 03 January 2022
Accepted Manuscript online:
03 January 2022
Article published online:
24 February 2022
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