Issue 11, 2021

Palladium-catalyzed 1,2-amino carbonylation of 1,3-dienes with (N-SO2Py)-2-iodoanilines: 2,3-dihydroquinolin-4(1H)-ones synthesis

Abstract

A palladium-catalyzed 1,2-amino carbonylation of 1,3-dienes with (N-SO2Py)-2-iodoanilines has been developed for the construction of 2,3-dihydroquinolin-4(1H)-one scaffolds. Using benzene-1,3,5-triyl triformate (TFBen) as the CO source under the assistance of the N-SO2Py directing group, the reaction proceeded well to afford various 2,3-dihydroquinolin-4(1H)-ones in good yields (up to 88%). The effect of the directing groups was investigated and control experiments were performed to have a better understanding of the reaction pathway.

Graphical abstract: Palladium-catalyzed 1,2-amino carbonylation of 1,3-dienes with (N-SO2Py)-2-iodoanilines: 2,3-dihydroquinolin-4(1H)-ones synthesis

Supplementary files

Article information

Article type
Research Article
Submitted
18 fev 2021
Accepted
12 mar 2021
First published
16 mar 2021

Org. Chem. Front., 2021,8, 2429-2433

Palladium-catalyzed 1,2-amino carbonylation of 1,3-dienes with (N-SO2Py)-2-iodoanilines: 2,3-dihydroquinolin-4(1H)-ones synthesis

J. Wang, Y. Na, J. Ying and X. Wu, Org. Chem. Front., 2021, 8, 2429 DOI: 10.1039/D1QO00290B

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