Issue 19, 2022

Selectfluor-mediated construction of 3-arylselenenyl and 3,4-bisarylselenenyl spiro[4.5]trienones via cascade annulation of N-phenylpropiolamides with diselenides

Abstract

A cascade annulation of terminal alkynyl amides with diselenides leading to the construction of 3-arylselenenyl spiro[4.5]trienones was realized under mild conditions with Selectfluor as the sole oxidant. Furthermore, 3,4-bisarylselenenyl spiro[4.5]trienones were also synthesized by a cascade annulation reaction using transition-metal copper as a catalyst. This spirocyclization process is suggested to encompass a sequential C(sp)–Se and C(sp)–C(sp2) bond formation with the concomitant introduction of a carbonyl oxygen.

Graphical abstract: Selectfluor-mediated construction of 3-arylselenenyl and 3,4-bisarylselenenyl spiro[4.5]trienones via cascade annulation of N-phenylpropiolamides with diselenides

Supplementary files

Article information

Article type
Paper
Submitted
20 Feb 2022
Accepted
15 Apr 2022
First published
19 Apr 2022

New J. Chem., 2022,46, 9451-9460

Selectfluor-mediated construction of 3-arylselenenyl and 3,4-bisarylselenenyl spiro[4.5]trienones via cascade annulation of N-phenylpropiolamides with diselenides

J. Yuan, Q. Chen, W. Wu, J. Zhao, L. Yang, Y. Xiao, P. Mao and L. Qu, New J. Chem., 2022, 46, 9451 DOI: 10.1039/D2NJ00869F

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