Transition-metal-free three-component acetalation-pyridylation of alkenes via photoredox catalysis

A general transition-metal-free photoinduced acetalation-pyridylation of alkenes using diethoxyacetic acid and cyanopyridine was developed under mild conditions. By employing 4CzIPN as the photocatalyst and Cs2CO3 as the base, a diverse range of styrene derivatives and cyanopyridines worked well to...

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Bibliographic Details
Published inChinese journal of catalysis Vol. 43; no. 3; pp. 571 - 583
Main Authors Ma, Chun-Hua, Ji, Yu, Zhao, Jie, He, Xing, Zhang, Shu-Ting, Jiang, Yu-Qin, Yu, Bing
Format Journal Article
LanguageEnglish
Published Elsevier B.V 01.03.2022
Subjects
Aldehyde
Antitumor
Diverse transformation
Late-stage modification
Visible-light promoted
Visible-light promoted
Aldehyde
Diverse transformation
Late-stage modification
Antitumor
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Summary:A general transition-metal-free photoinduced acetalation-pyridylation of alkenes using diethoxyacetic acid and cyanopyridine was developed under mild conditions. By employing 4CzIPN as the photocatalyst and Cs2CO3 as the base, a diverse range of styrene derivatives and cyanopyridines worked well to give the desired products. The versatility of this method is highlighted by its application in the construction of various functional groups and the late-stage modification of drugs. Importantly, some of the synthesized compounds showed good in vitro antitumor activity, indicating that this protocol is of significance and potential for antitumor drug development. The acetalation-pyridylation of alkenes was achieved in the visible-light promoted protocol, and diverse group transformations were achieved in simple operation. It could provide hit compounds for antitumor drug development.
ISSN:1872-2067
1872-2067
DOI:10.1016/S1872-2067(21)63917-7