A Convenient Method of Amidation of Carboxylic Acids Using Boron Trifluoride Etherate

Tani, Junichi; Oine, Toyonari; Inoue, Ichizo

doi:10.1055/s-1975-23900

Cited by 46 publications

(13 citation statements)

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“…The first publication of arylboronic acid catalyzed amide bond formation was a communication by Yamamoto in 1996. [20] Reactions employing stoichiometric amounts of boron reagents to affect amidation were known, [42,43] yet they were limited by a lack of turnover owing to the production of inactive boron species. While Yamamoto originally proposed a mechanism that involved formation of mixed anhydrides including an initial cyclotrimeric boroxine (1) and an (aclyoxy)boron intermediate (2) that enabled dehydrative coupling (Figure 2), the mechanism of boronic acid catalyzed amidation has been since studied extensively [44] and found to be significantly more complex and to not actually involve (2).…”

Section: Alternative Approaches To Noncanonical Amidationmentioning

confidence: 99%

Recent developments in catalytic amide bond formation

Todorovic

Perrin

2020

Peptide Science

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Amide bond forming reactions are critical for both polypeptide synthesis and medicinal chemistry. Most current approaches for amidation employ stoichiometric activating agents, but such methods are neither atom economical nor synthetically elegant. Catalytic approaches for amidation are potentially green and more ideal substitutes for current standard methods and thus are the subject of this review. Such methods face significant thermodynamic and kinetic barriers and have, as a result, historically

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Section: Alternative Approaches To Noncanonical Amidationmentioning

confidence: 99%

Recent developments in catalytic amide bond formation

Todorovic

Perrin

2020

Peptide Science

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“…Subsequently, the direct formation of amides with the aid of a variety of boron reagents including BF 3 ·OEt 2 , [25] borane, [26] catechol borane [27] and tris-(dialkylamino)boranes [28] has been reported. However, these reagents require anhydrous reaction conditions due to the sensitivity of the reagents towards moisture, and in some cases an excess either of the amine or of the carboxylic acid is also needed.…”

Section: Amidation Of Carboxylic Acidsmentioning

confidence: 99%

Recent Developments in Amide Synthesis: Direct Amidation of Carboxylic Acids and Transamidation Reactions

Lanigan¹,

Sheppard²

2013

Eur J Org Chem

362

153

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The synthesis of amides is of huge importance in a wide variety of industrial and academic fields and is of particular significance in the synthesis of pharmaceuticals. Many of the well established methods for amide synthesis involve reagents that are difficult to handle and lead to the generation of large quantities of waste products. As a consequence, there has been a considerable amount of interest in the development of new approaches to amide synthesis. Over the past few years a wide range of new reagents and catalysts for direct amidation of carboxylic acids have been reported. In addition, the interconversion of amide derivatives through transamidation is emerging as a potential alternative strategy for accessing certain amides. This microreview covers recent developments in the direct amidation of carboxylic acids and the interconversion of amides through transamidation. The advantages and disadvantages of the various methods are discussed, as well as the possible mechanisms of the reactions.

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“…However, this method is not effective for aromatic substrates such as benzoic acids and anilines. (Acyloxy)boron intermediates generated from carboxylic acids and boron reagents such as BR 3 (R¼C 8 H 17 , OMe) [19], ClB (OMe) 2 [19], HB(OR) 2 (R¼i-Pr, t-Am) [19], BH 3 • R 3 N (R¼Me, Bu) [20], BF 3 • Et 2 O [21], and catecholborane [22] were shown to react with amines to furnish amides in moderate to good yields, but only under uniformly stoichiometric reaction conditions. In these boron-mediated amidations, boron reagents transform into inactive boron species after the reaction of (acyloxy)boron derivatives and amines.…”

Section: B(iii)-catalyzed Reactions Of αβ-Unsaturatedmentioning

confidence: 99%

Boronic Acid-Catalyzed Reactions of Carboxylic Acids

Ishihara

2015

Topics in Organometallic Chemistry

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A Convenient Method of Amidation of Carboxylic Acids Using Boron Trifluoride Etherate

Cited by 46 publications

References 0 publications

Recent developments in catalytic amide bond formation

Recent developments in catalytic amide bond formation

Recent Developments in Amide Synthesis: Direct Amidation of Carboxylic Acids and Transamidation Reactions

Boronic Acid-Catalyzed Reactions of Carboxylic Acids

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