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Ruthenium‐Catalyzed Synthesis of Isoindolinones via Amide‐Directed Addition of Aromatic C‐H Bonds to Aldimines
Author(s) -
Miura Hiroki,
Kimura Yuriko,
Terajima Sachie,
Shishido Tetsuya
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801755
Subject(s) - aldimine , chemistry , catalysis , amide , substituent , ruthenium , aryl , medicinal chemistry , yield (engineering) , organic chemistry , combinatorial chemistry , alkyl , materials science , metallurgy
Ruthenium‐catalyzed addition of aromatic C‐H bonds to aldimines is described. [RuCl 2 ( p ‐cymene)] 2 functions as an efficient catalyst to promote the coupling of aryl amides with aldimines in the presence of a catalytic amount of base to give the corresponding isoindolinone derivatives. The nature of the substituent at the N ‐atom of the amides is crucial for the efficient conversion of the substrates, and a p ‐toluenesulfonyl group is the functionality of choice. A variety of amides and aldimines participated in the present Ru‐catalyzed reaction to furnish the corresponding isoindolinones in moderate to high yield.