Palladium-Catalyzed Synthesis of β-Lactams via Carbonylative Cycloaddition of Benzyl and Allyl Halides with Imines

Synthesis of 1,3-diaryl-spiro[azetidine-2,3′-indoline]-2′,4-dionesviathe Staudinger reaction:cis- ortrans-diastereoselectivity with different addition modes

“…1 Spiro-oxindoles SAR405838 and APG-115, 16,17 which are currently under clinical trials, and dispiro-oxindole KM-140 have successfully completed preclinical studies. 10,19 cyclization of N-(p-hydroxyphenyl) cyanoacetamides, 25 the intramolecular N-alkylation of amides, 26 the Kinugasa reaction ([3 + 2] nitrones cycloaddition to acetylenide followed by acid-catalyzed rearrangement to b-lactam), [27][28][29] the Pd-catalyzed carbonylation of allyl halides followed by the reaction with imines, [30][31][32][33] the cyclization of b-amino acid esters, [34][35][36][37] and Staudinger's keteneimine cycloaddition. [38][39][40] Staudinger synthesis is the most common method and can be carried out using various synthetic techniques with a well-established mechanism.…”

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]. Among them, in connection with this report, 2-bromobenzaldehydes [17] and ␤-bromovinyl aldehydes [18] were found to be aromatized with suitably functionalized alkenes in the presence of a palladium catalyst to afford naphthalenes and benzenes, respectively.…”

A Practical Palladium-Catalysed Heteroannulation of 2-bromobenzaldehyde with Alcohols and Carbon Monoxide Leading to 3-alkoxy-3H-isobenzofuran-1-ones

“…1 In connection with this report, homogeneous transition metal-catalysed synthetic methods have also been attempted for the formation of 3H-isobenzofuran-1-one (phthalide) 2 since several phthalide-containing compounds exert a broad spectrum of physiological activities. 3 During the course of our ongoing studies on palladium-catalysed carbonylative cyclisation reactions, 4,5 we recently reported a synthetic method for the formation of 3-substituted phthalides from 2-bromobenzaldehyde and nucleophiles such as aliphatic alcohols, 6 phenols, 7 1,3-dicarbonyl compounds, 8 sodium alkanoates 9 and carboxylic acids. 10 In the reaction with aliphatic alcohols, because the alcohols were used as solvent as well as nucleophile, the reaction using higher boiling alcohols has a drawback which is the difficulty of separation of the product from the reaction mixture.…”