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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

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

Toshikatsu Maki, Kazuaki Ishihara, Hisashi Yamamoto

Org Lett. 2006 Mar 30;8(7):1431-4.

PMID: 16562909

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP73852194	3,5-Bis(trifluoromethyl)phenylboronic acid		73852-19-4	Price

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