Synthesis of 3-Substituted 4-Aroylisoquinolines via Pd-Catalyzed Carbonylative Cyclization of o-(1-Alkynyl)benzaldimines

Abstract

[reaction: see text] o-(1-Alkynyl)benzaldimines react with aryl iodides and 1 atm of CO in the presence of tri-n-butylamine and a Pd(PPh(3))(4) catalyst to afford good yields of 3-substituted 4-aroylisoquinolines by acylpalladation of the carbon-carbon triple bond and cyclization.

Six‐Membered Heterocycles: Quinoline and Isoquinoline

“…The former methodology was subsequently expanded to the synthesis of 3-substituted-4-aroylisoquinolines 184 by palladium-catalyzed carbonylative cyclization of 2-(1-alkynyl)benzaldimines 185 and aryl halides (Scheme 17.112) [314,315]. The reaction is useful for both electron-rich and electron-poor aryl halides.…”

Synthesis of heterocycles by carbonylation of acetylenic compounds

“…46,47 The authors proposed, 46,47 that the mechanism of this process (Scheme 26) includes the following key steps: (1) oxidative addition of the aryl halide to the Pd 0 catalyst, followed by CO insertion;…”

A new route for isoquinolines catalyzed by palladium

“…Thus, besides conventional named routes such as Bischler-Napieralski, PictetSpengler [1] and Pomeranz-Fritsch syntheses [2], homogeneous palladium-catalyzed synthetic methods have also been developed as alternative methods for the construction of isoquinoline framework because of efficiency of reaction and wide availability of substrates [3][4][5][6][7][8][9]. As part of our continuing studies directed towards transition metal-catalyzed cyclization reactions, we recently reported on palladium-catalyzed synthesis of various carbo-and heterocycles [10][11][12][13][14][15][16].…”