An unexpected synthesis of azepinone derivatives through a metal-free photochemical cascade reaction

Lina Song, Xianhai Tian*, Kaveh Farshadfar, Farshad Shiri, Frank Rominger, Alireza Ariafard*, A. Stephen K. Hashmi*

*Tämän työn vastaava kirjoittaja

Tutkimustuotos: LehtiartikkeliArticleScientificvertaisarvioitu

10 Sitaatiot (Scopus)
48 Lataukset (Pure)

Abstrakti

Azepinone derivatives are privileged in organic synthesis and pharmaceuticals. Synthetic approaches to these frameworks are limited to complex substrates, strong bases, high power UV light or noble metal catalysis. We herein report a mild synthesis of azepinone derivatives by a photochemical generation of 2-aryloxyaryl nitrene, [2 + 1] annulation, ring expansion/water addition cascade reaction without using any metal catalyst. Among the different nitrene precursors tested, 2-aryloxyaryl azides performed best under blue light irradiation and Brønsted acid catalysis. The reaction scope is broad and the obtained products underwent divergent transformations to afford other related compounds. A computational study suggests a pathway involving a step-wise aziridine formation, followed by a ring-expansion to the seven-membered heterocycle. Finally, water is added in a regio-selective manner, this is accelerated by the added TsOH.

AlkuperäiskieliEnglanti
Artikkeli831
Sivumäärä8
JulkaisuNature Communications
Vuosikerta14
Numero1
DOI - pysyväislinkit
TilaJulkaistu - 14 helmik. 2023
OKM-julkaisutyyppiA1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

Sormenjälki

Sukella tutkimusaiheisiin 'An unexpected synthesis of azepinone derivatives through a metal-free photochemical cascade reaction'. Ne muodostavat yhdessä ainutlaatuisen sormenjäljen.

Siteeraa tätä