Palladium-Catalyzed Cascade Carbonylative Synthesis of Perfluoroalkyl and Carbonyl-Containing 3,4-Dihydroquinolin-2(1 H)-one Derivatives

Shangyuan Wang; Jiangjie Zhang; Jian-Shu Wang; Jun Ying; Xiao-Feng Wu

doi:10.1021/acs.orglett.2c03636

Palladium-Catalyzed Cascade Carbonylative Synthesis of Perfluoroalkyl and Carbonyl-Containing 3,4-Dihydroquinolin-2(1 H)-one Derivatives

Org Lett. 2022 Dec 9;24(48):8843-8847. doi: 10.1021/acs.orglett.2c03636. Epub 2022 Nov 24.

Authors

Shangyuan Wang¹, Jiangjie Zhang¹, Jian-Shu Wang¹, Jun Ying¹, Xiao-Feng Wu^{2

3}

Affiliations

¹ Department of Chemistry, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou 310018, China.
² Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 116023 Dalian, Liaoning, China.
³ Leibniz-Institut für Katalyse e.V., Albert-Einstein-Straβe 29a, 18059 Rostock, Germany.

PMID: 36421178
DOI: 10.1021/acs.orglett.2c03636

Abstract

A palladium-catalyzed cascade radical cyclization and carbonylation of 1,7-enynes with perfluoroalkyl iodides and alcohols has been described. This procedure provides a facile and efficient approach for the construction of 3,4-dihydroquinolin-2(1H)-one skeletons by using benzene-1,3,5-triyl triformate (TFBen) as the CO source. This method enables the incorporation of both perfluoroalkyl and carbonyl units into the 3,4-dihydroquinolin-2(1H)-one skeletons, producing a variety of 3,4-dihydroquinolin-2(1H)-one derivatives in moderate to high yields and with excellent E/Z selectivity.