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The Ortho-Substituent on 2,4-bis(trifluoromethyl)phenylboronic Acid Catalyzed Dehydrative Condensation Between Carboxylic Acids and Amines

The Ortho-Substituent on 2,4-bis(trifluoromethyl)phenylboronic Acid Catalyzed Dehydrative Condensation Between Carboxylic Acids and Amines

Ke Wang, Yanhui Lu, Kazuaki Ishihara

Chem Commun (Camb). 2018 May 24;54(43):5410-5413.

PMID: 29714375

Abstract:

2,4-Bis(trifluoromethyl)phenylboronic acid is a highly effective catalyst for dehydrative amidation between carboxylic acids and amines. Mechanistic studies suggest that a 2 : 2 mixed anhydride is expected to be the only active species, and the ortho-substituent of boronic acid plays a key role in preventing the coordination of amines to the boron atom of the active species, thus accelerating the amidation. This catalyst works for α-dipeptide synthesis.

Chemicals Related in the Paper:

Catalog Number	Product Name	CAS Number	Price
AP128796394	4-(Trifluoromethyl)phenylboronic acid	128796-39-4	Price
AP153254092	2,4-Bis(trifluoromethyl)phenylboronic acid	153254-09-2	Price
AP870777212	2-(2′-Chlorobenzyloxy)phenylboronic acid	870777-21-2	Price
LS793645	(4-benzyloxy-2-formyl)phenylboronic acid		Price
LS793966	3-(4-oxopiperidine-1-carbonyl)phenylboronic acid		Price

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