Intramolecular dehydrative condensation of dicarboxylic acids with brnsted base-assisted boronic acid catalysts

Akira Sakakura, Risa Yamashita, Takuro Ohkubo, Matsujiro Akakura, Kazuaki Ishihara

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Bifunctional Brnsted base-assisted boronic acid catalysts, arylboronic acids bearing two sterically bulky (N,N-dialkylamino)methyl groups at the 2,6-positions, exhibit remarkable activities for the dehydrative intramolecular condensation of dicarboxylic acids. The steric bulkiness of the (N,N-dialkylamino)methyl groups of 1, which prevents the formation of less active species such as the N→B chelated species and triarylboroxines 3, is crucial for the high catalytic activity. This is the first successful method for the catalytic dehydrative self-condensation of di-and tetracarboxylic acids.

Original languageEnglish
Pages (from-to)1458-1465
Number of pages8
JournalAustralian Journal of Chemistry
Volume64
Issue number11
DOIs
Publication statusPublished - 2011
Externally publishedYes

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Boronic Acids
Dicarboxylic Acids
Condensation
Bearings (structural)
Catalysts
Acids
Catalyst activity

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Intramolecular dehydrative condensation of dicarboxylic acids with brnsted base-assisted boronic acid catalysts. / Sakakura, Akira; Yamashita, Risa; Ohkubo, Takuro; Akakura, Matsujiro; Ishihara, Kazuaki.

In: Australian Journal of Chemistry, Vol. 64, No. 11, 2011, p. 1458-1465.

Research output: Contribution to journalArticle

Sakakura, Akira ; Yamashita, Risa ; Ohkubo, Takuro ; Akakura, Matsujiro ; Ishihara, Kazuaki. / Intramolecular dehydrative condensation of dicarboxylic acids with brnsted base-assisted boronic acid catalysts. In: Australian Journal of Chemistry. 2011 ; Vol. 64, No. 11. pp. 1458-1465.
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