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Chelating Group Enabled Palladium‐Catalyzed Regiodivergent Carbonylative Synthesis of 2,3‐Dihydroquinolin‐4(1 H )‐ones
Author(s) -
Ying Jun,
Wang JianShu,
Yao Lingyun,
Lu Wangyang,
Wu XiaoFeng
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202003003
Subject(s) - palladium , aryl , chemistry , catalysis , benzene , chelation , alkyl , sulfonyl , medicinal chemistry , alkene , combinatorial chemistry , organic chemistry
A new procedure on palladium‐catalyzed carbonylative cyclization of N‐ (2‐pyridyl)sulfonyl ( N ‐SO 2 Py)‐2‐iodoanilines with terminal alkenes has been developed for the rapid construction of dihydroquinolin‐4(1 H )‐one scaffolds. Enabled by the chelating group and using benzene‐1,3,5‐triyl triformate (TFBen) as the CO source, both aromatic and aliphatic alkenes were smoothly transformed into the corresponding 2,3‐dihydroquinolin‐4(1 H )‐ones in good yields with excellent regioselectivities. Notably, the reaction of aromatic alkenes produces 2‐aryl‐2,3‐dihydroquinolin‐4(1 H )‐ones, while 3‐alkyl‐2,3‐dihydroquinolin‐4(1 H )‐ones were obtained when aliphatic alkenes were used. This protocol has been applied in the synthesis of antitumor agent A as well.