4,5,6,7-Tetrachlorobenzo[d][1,3,2]dioxaborol- 2-ol as an effective catalyst for the amide condensation of sterically demanding carboxylic acids.

doi:10.1021/OL060216R

Paper

4,5,6,7-Tetrachlorobenzo[d][1,3,2]dioxaborol- 2-ol as an effective catalyst for the amide condensation of sterically demanding carboxylic acids.

Published Mar 4, 2006 · T. Maki, K. Ishihara, Hisashi Yamamoto

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Abstract

[reaction: see text] 4,5,6,7-Tetrachlorobenzo[d][1,3,2]dioxaborole (4a) and 4,5,6,7-tetrachlorobenzo[d][1,3,2]dioxaborol-2-ol (4b) are effective catalysts for the dehydrative amide condensation between an equimolar mixture of carboxylic acids and amines. In particular, these catalysts are greatly superior to 3,5-bis(trifluoromethyl)phenylboronic acid (1) for the amide condensation of sterically demanding carboxylic acids. In contrast, 4c, which is prepared from a 1:2 molar mixture of B(OH)(3) and tetrachlorocatechol, is effective as a Lewis acid-assisted Brønsted acid (LBA) catalyst for Ritter reaction.

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4,5,6,7-Tetrachlorobenzo[d][1,3,2]dioxaborole and 4,5,6,7-Tetrachlorobenzo[d][1,3,2]dioxaborol-2-ol are effective catalysts for the amide

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

4,5,6,7-Tetrachlorobenzo[d][1,3,2]dioxaborol- 2-ol as an effective catalyst for the amide condensation of sterically demanding carboxylic acids.

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References

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Citations

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This study presents a catalytic methodology for synthesizing N-methyl secondary amides using diboronic acid anhydride, which can be applied to the synthesis of biologically active compounds like halostachine, synephrine, and phenylephrine.

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Organoboron catalysis offers an environmentally friendly, energy-saving, and safe method for synthesizing amides, benefiting life and material sciences.

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Diphenyl carbonate-mediated amide synthesis is a novel, one-pot method for the synthesis of drug molecules and intermediates, with potential applications in acetaminophen, moclobemide, vorinostat, and glipizide.