Carboxamides from Carboxylic Acids by Lewis Acid Catalysis. Use of Principal Properties for Exploring Different Reaction Conditions.

Nordahl, Åke; Carlson, Rolf; Rømming, Christian; Skattebøl, Lars; Karjalainen, Arto; Berg, Jan-Eric; Bartók, Mihály; Pelczer, István; Dombi, György

doi:10.3891/acta.chem.scand.42b-0028

Cited by 20 publications

(6 citation statements)

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“…Example: Lewis Acid-Mediated Synthesis of Benzamides. This example is taken from ref . Carboxamides can be prepared by a large number of methods.…”

Section: Exploring the Reaction Spacementioning

confidence: 99%

“…The following test solvents were selected from the principal property score plot so that they afforded a maximum spread (diversity) design. The following solvents were chosen (the numbers refer to the score plot in Figure 2): formamide (2), sulfolane (28), 1,2-dichlorobenzene (57), cyclohexane (81), tetrahydrofuran (63), methoxyethanol (8), methanol (4), 2-methyl-2-butanol (40), and diethylene glycol (6).…”

Section: Exploring the Reaction Spacementioning

confidence: 99%

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Principal Properties and Designs for Discrete Variations¹

Carlson

2005

Org. Process Res. Dev.

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A problem that is often encountered when a new synthetic reaction is developed is to determine suitable combinations of reagents, co-reagents, catalysts, solvents, etc. This contribution presents general strategies for designing experiments when the objective is to explore the discrete variations defined by different reagents, different catalysts, different solvents, etc. The concept of principal properties is introduced, and it is shown how the principal properties of the constituents of the reaction system can be used for the selection of suitable test systems. Chemical examples are provided by the following: the selection of test solvents in the reduction of an enamine; the selection of combinations of Lewis acids and amines in the synthesis of benzamides; the selection of ketone substrates, amines, and solvents in the Willgerodt−Kindler reaction; and the selection of ketone substrates, Lewis acid catalysts, and solvents for analysing the regioselectivity in the Fischer indole synthesis with dissymmetric ketones.

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“…Example: Lewis Acid-Mediated Synthesis of Benzamides. This example is taken from ref . Carboxamides can be prepared by a large number of methods.…”

Section: Exploring the Reaction Spacementioning

confidence: 99%

Section: Exploring the Reaction Spacementioning

confidence: 99%

Principal Properties and Designs for Discrete Variations¹

Carlson

2005

Org. Process Res. Dev.

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“…Later carboxyamides from benzoic acids and different amines were obtained by using stochiometric amounts of various Lewis acid catalysts in refluxing toluene [ 26 ].…”

Section: Introductionmentioning

confidence: 99%

Formation of amides: one-pot condensation of carboxylic acids and amines mediated by TiCl4

Leggio

Bagalà

Belsito

et al. 2017

Chemistry Central Journal

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A general procedure for the synthesis of amides via the direct condensation of carboxylic acids and amines in the presence of TiCl4 is reported. The amidation reaction was performed in pyridine at 85 °C with a wide range of substrates providing the corresponding amide products in moderate to excellent yields and high purity. The reaction proceeds with low yields when both the carboxylic acid and the amine are sterically hindered. The process takes place with nearly complete preservation of the stereochemical integrity of chiral substrates.Electronic supplementary materialThe online version of this article (doi:10.1186/s13065-017-0318-9) contains supplementary material, which is available to authorized users.

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“…Selection of Lewis acids by their principal properties for synthetic exploration has been reported for syntheses of benzamides [59], of silyloxydienes [33], and of indoles [60].…”

Section: Lewis Acids [51]mentioning

confidence: 99%

“…5.3.2 where a design with 600 systems whs obtained in this way. Other examples which have been presented in the literature are the synthesis of benzamide by the direct reaction between benzoic acid and amines in the presence of a Lewis acid [59] where it was found that the proper choice of Lewis acid was dependent on the nature of the amine; and the synthesis of silyl enol ehters where an initial screening based upon these principles made it possible to find an optimal combination of reagent and solvent [33].…”

Section: Use a Statistical Design To Explore Several Dimensions Of Thmentioning

confidence: 99%

Exploring organic synthetic experimental procedures

Carlson

Nordahl

Topics in Current Chemistry

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Carboxamides from Carboxylic Acids by Lewis Acid Catalysis. Use of Principal Properties for Exploring Different Reaction Conditions.

Cited by 20 publications

References 0 publications

Principal Properties and Designs for Discrete Variations¹

Principal Properties and Designs for Discrete Variations¹

Formation of amides: one-pot condensation of carboxylic acids and amines mediated by TiCl4

Exploring organic synthetic experimental procedures

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Carboxamides from Carboxylic Acids by Lewis Acid Catalysis. Use of Principal Properties for Exploring Different Reaction Conditions.

Cited by 20 publications

References 0 publications

Principal Properties and Designs for Discrete Variations1

Principal Properties and Designs for Discrete Variations1

Formation of amides: one-pot condensation of carboxylic acids and amines mediated by TiCl4

Exploring organic synthetic experimental procedures

Contact Info

Product

Resources

About

Principal Properties and Designs for Discrete Variations¹

Principal Properties and Designs for Discrete Variations¹