Boronic Acid-Catalyzed Reactions of Carboxylic Acids

Ishihara, Kazuaki

doi:10.1007/978-3-319-13054-5_8

Cited by 21 publications

(1 citation statement)

References 56 publications

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“…In 1996, Yamamoto and co-workers reported the first catalytic amidation using electron-deficient arylboronic acids (Figure , B1) . Since then, more modified aromatic boronic acid catalysts were developed by several groups (Figure ), representing greener protocols in the synthesis of amide derivatives. Even though much progress has been achieved in this area, most examples focused on limited substrate types, and the synthesis of boron catalysts has been becoming ever more complex.…”

Section: Introductionmentioning

confidence: 99%

Heterocyclic Boron Acid Catalyzed Dehydrative Amidation of Aliphatic/Aromatic Carboxylic Acids with Amines

et al. 2023

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Section: Introductionmentioning

confidence: 99%

Heterocyclic Boron Acid Catalyzed Dehydrative Amidation of Aliphatic/Aromatic Carboxylic Acids with Amines

et al. 2023

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Design of Boronic Acid–Base Complexes as Reusable Homogeneous Catalysts in Dehydrative Condensations between Carboxylic Acids and Amines

Wang

Ishihara

2017

Asian J Org Chem

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Twon ovel boronic acid-base complexesw ere developed as reusable homogeneous catalysts for amide condensation. First, quaternary ammonium resin-bound boronates were shown to be effective catalysts that might release free boronic acids during reactions and could be regenerateda fterwards. Next, a1 :1 mixture of 3,5-dinitro-4-tolueneboronic acid and4 -(N,N-dimethylamino)pyridine N-oxide (DMAPO) or 4-(N,N,-dimethylamino)pyridine (DMAP) cooperativelypromoted amide formationa nd precipitated as an acid-base solid complex after cooling. These inexpensive and reusablec omplexes may be useful in large-scale process chemistry.

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Enantioselective 1,4‐Addition Reaction of α,β‐Unsaturated Carboxylic Acids with Cycloalkanones Using Cooperative Chiral Amine–Boronic Acid Catalysts

et al. 2020

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An enantioselective 1,4‐addition of α,β‐unsaturated carboxylic acids with cycloalkanones has been developed by using chiral amine–boronic acid cooperative catalysts. In the presence of a chiral amine and boronic acid, cycloalkanones and carboxylic acids are activated as chiral enamines and mixed anhydrides, respectively. The corresponding 1,4‐adducts are obtained in high yield with high enantioselectivity. Furthermore, subsequent oxylactonization of the 1,4‐adducts gives spirolactones with high diastereoselectivity.

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Boronic Acid-Catalyzed Reactions of Carboxylic Acids

Cited by 21 publications

References 56 publications

Heterocyclic Boron Acid Catalyzed Dehydrative Amidation of Aliphatic/Aromatic Carboxylic Acids with Amines

Heterocyclic Boron Acid Catalyzed Dehydrative Amidation of Aliphatic/Aromatic Carboxylic Acids with Amines

Design of Boronic Acid–Base Complexes as Reusable Homogeneous Catalysts in Dehydrative Condensations between Carboxylic Acids and Amines

Enantioselective 1,4‐Addition Reaction of α,β‐Unsaturated Carboxylic Acids with Cycloalkanones Using Cooperative Chiral Amine–Boronic Acid Catalysts

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