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

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 annula...

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Veröffentlicht in:New journal of chemistry 2022-04, Vol.46 (19), p.9451-9460
Hauptverfasser: Yuan, Jin-Wei, Chen, Qian, Wu, Wen-Tao, Zhao, Jian-Jun, Yang, Liang-Ru, Xiao, Yong-Mei, Mao, Pu, Qu, Ling-Bo
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Sprache:eng
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Zusammenfassung: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(sp 2 ) bond formation with the concomitant introduction of a carbonyl oxygen.
ISSN:1144-0546
1369-9261
DOI:10.1039/D2NJ00869F