Palladium-catalyzed carbonylation of aryl triplates. Synthesis of arenecarboxylic acid derivatives from phenols

Cacchi, Sandro; Ciattini, Pier Giuseppe; Morera, Enrico; Ortar, Giorgio

doi:10.1016/s0040-4039(00)83920-9

Cited by 152 publications

(45 citation statements)

References 13 publications

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“…[1,2] Among the aryl halides, aryl chlorides are particularly attractive starting materials for these transformations, as they are both inexpensive and commercially abundant. [3] The relative chemical inertness of the aryl chlorides also makes them more challenging substrates, [3] and aryl chloride carbonylation methodologies remain underdeveloped compared to those of the more expensive aryl bromide, [4] iodide, [5] and triflate [6] variants.…”

mentioning

confidence: 99%

Palladium‐Catalyzed Aminocarbonylation of Aryl Chlorides at Atmospheric Pressure: The Dual Role of Sodium Phenoxide

et al. 2007

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confidence: 99%

Palladium‐Catalyzed Aminocarbonylation of Aryl Chlorides at Atmospheric Pressure: The Dual Role of Sodium Phenoxide

et al. 2007

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“…This direct procedure is superior to the strategy via the corresponding carboxylic acid ester intermediates [22,23].…”

Section: Chemistrymentioning

confidence: 94%

Cyclohex‐1‐ene Carboxylic Acids: Synthesis and Biological Evaluation of Novel Inhibitors of Human 5α Reductase

Baston

Hartmann

2003

Archiv der Pharmazie

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In search of novel nonsteroidal mimics of steroidal inhibitors of 5 alpha reductase, 4-(2-phenylethyl)cyclohex-1-ene carboxylic acids 1-5 were synthesized with different substituents in para position of the phenyl ring (1: N, N-diisopropylcarbamoyl, 2: phenyl, 3: phenoxy, 4: benzoyl, and 5: benzyl). The principal synthetic approach for the desired compounds consisted of a Wittig olefination between 1, 4-dioxaspiro [4.5]-decane-8-carbaldehyde (4g and the appropriate phosphonium salts. The compounds were tested for inhibition of human 5 alpha reductase isozymes 1 and 2 using DU 145 cells and preparations from prostatic tissue, respectively. They turned out to be good inhibitors of the prostatic isozyme 2 with compound 1 being the most potent one (IC(50) = 760 nM). Isozyme 1 was only slightly inhibited. It is concluded that the novel structures are appropriate for being further optimized, aiming at the development of a novel drug for the treatment of benign prostatic hyperplasia.

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“…General procedure for aminocarbonylation of steroidal iodoalkenes 2 and 5 at high carbon monoxide pressure A mixture of 17-iodo-3-ethylene ketal (2) [or 3-iodo-17-ethylene ketal derivative (5)] (1 mmol), 5.6 mg palladium(II) acetate (0.025 mmol), and 13.1 mg PPh 3 (0.05 mmol) were dissolved in 15 cm 3 dimethylformamide under argon. Et 3 N (0.5 cm 3 ) and 33.5 mm 3 ethylene diamine (0.5 mmol) (or another diamine) as N-nucleophile were added.…”

Section: Methodsmentioning

confidence: 99%

“…The introduction of the carboxamide functionality either to the A-or the D-ring at the distinguished position 3 and 17, resulted in the synthesis of potential 5a-reductase inhibitors [2][3][4][5][6][7]. One of the most challenging ways to introduce the carboxamide functionality is the facile palladium-catalyzed aminocarbonylation reaction.…”

Section: Introductionmentioning

confidence: 99%

Palladium-catalyzed diaminocarbonylation: synthesis of androstene dimers containing 3,3′- or 17,17′-dicarboxamide spacers

et al. 2014

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Novel androstene-based dimers linked through A-and D-ring with 3,3 0 -and 17,17 0 -dicarboxamide spacers, were synthesized via palladium-catalyzed aminocarbonylation. Androstane derivatives possessing either 3-iodo-3,5-diene or 17-iodo-16-ene functionality were used as substrates in the presence of palladium-phosphine in situ catalysts and aliphatic and aromatic diamines as N-nucleophiles. Since androst-4-ene-3,17-dione was used as starting material, a multistep synthesis including protection/deprotection of one of the keto functionalities (3-one or 17-one) as ethylene ketals, transformation of the other keto group to iodoalkene functionality via its hydrazone, and palladium-catalyzed aminocarbonylation of the iodoalkene functionality was used. In this way, new dimeric compounds possessing a keto functionality were obtained in moderate-to-good isolated yields, via highly chemoselective reactions, under relatively mild conditions.

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Palladium-catalyzed carbonylation of aryl triplates. Synthesis of arenecarboxylic acid derivatives from phenols

Cited by 152 publications

References 13 publications

Palladium‐Catalyzed Aminocarbonylation of Aryl Chlorides at Atmospheric Pressure: The Dual Role of Sodium Phenoxide

Palladium‐Catalyzed Aminocarbonylation of Aryl Chlorides at Atmospheric Pressure: The Dual Role of Sodium Phenoxide

Cyclohex‐1‐ene Carboxylic Acids: Synthesis and Biological Evaluation of Novel Inhibitors of Human 5α Reductase

Palladium-catalyzed diaminocarbonylation: synthesis of androstene dimers containing 3,3′- or 17,17′-dicarboxamide spacers

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