Synthesis of nitrogen-tethered 1,6-enynes through CuI/TFA catalysis

A novel method for the concise and effective construction of nitrogen-tethered 1,6-enynes in moderate to good yields was developed. This transformation involves a TFA-promoted Pictet-Spengler reaction/iminium formation, copper-catalyzed alkyne-iminium ene reaction/alkynylation of a 2-arylethan-1-amine, formaldehyde solution, and a terminal alkyne. The process features exclusive chemoselectivity, simple operation, and high atom economy. Preliminary experimental studies suggest that the alkyne-iminium ene reaction involving an intermolecular hydride transfer is the key step in the current methodology. © the Partner Organisations.

Authors
Cao L.1 , Huang L.1 , Xu X. 2 , Van Der Eycken E.V. , Feng H. 1, 4
Journal
Organic Chemistry Frontiers
Publisher
Royal Society of Chemistry
Number of issue
2
Language
English
Pages
394-399
Status
Published
Link
External link
DOI
10.1039/d1qo01358k
Volume
9
Year
2022
Organizations
  • 1 College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai, 201620, China
  • 2 Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven, B-3001, Belgium
  • 3 Shanghai Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya Street 6, Moscow, 117198, Russian Federation
  • 4 Shanghai Frontiers Science Research Center for Druggability of Cardiovascular Noncoding RNA, Institute for Frontier Medical Technology, Shanghai University of Engineering Science, Shanghai, 201620, China
Keywords
Catalysis; Hydrocarbons; Alkynylations; Chemo-selectivity; Copper catalyzed; Ene reaction; Formaldehyde solutions; Iminium; Novel methods; Pictet-Spengler reactions; Simple operation; Terminal alkyne; Nitrogen
Date of creation
06.07.2022
Date of change
06.07.2022
Short link
https://repository.rudn.ru/en/records/article/record/83925/
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