Diboronic Acid Anhydrides as Effective Catalysts for the Hydroxy-Directed Dehydrative Amidation of Carboxylic Acids

The direct catalytic dehydrative amidation of β-hydroxycarboxylic acids with amines is described. A biphenyl-based diboronic acid anhydride with a B–O–B skeleton is shown to be an exceptionally effective catalyst for the reaction, providing β-hydroxycarboxylic amides in high to excellent yields with...

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Bibliographic Details
Published in:Organic letters 2019-06, Vol.21 (11), p.4303-4308
Main Authors: Shimada, Naoyuki, Hirata, Mai, Koshizuka, Masayoshi, Ohse, Naoki, Kaito, Ryoto, Makino, Kazuishi
Format: Article
Language:English
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Summary:The direct catalytic dehydrative amidation of β-hydroxycarboxylic acids with amines is described. A biphenyl-based diboronic acid anhydride with a B–O–B skeleton is shown to be an exceptionally effective catalyst for the reaction, providing β-hydroxycarboxylic amides in high to excellent yields with a low catalyst loading (minimum of 0.01 mol %, TON up to 7,500). This hydroxy-directed amidation shows excellent chemoselectivity and is applicable to gram-scale drug synthesis.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01484