Catalytic dehydrative amide bond formation using aqueous ammonia: synthesis of primary amides utilizing diboronic acid anhydride catalysis-Reference-Cited by-同舟云学术

Catalytic dehydrative amide bond formation using aqueous ammonia: synthesis of primary amides utilizing diboronic acid anhydride catalysis

Published:2023 Issue:48 Volume:59 Page:7391-7394
ISSN:1359-7345
Container-title:Chemical Communications
language:en
Short-container-title:Chem. Commun.

Author:

Takahashi Naoya¹,Iwasawa Hinata²,Kinashi Tatsuhito¹,Makino Kazuishi¹^ORCID,Shimada Naoyuki²^ORCID

Affiliation:

1. Laboratory of Organic Chemistry for Drug Development and Medical Research Laboratories, Department of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minatao-ku, Tokyo 108-8641, Japan

2. Laboratory of Organic Chemistry for Molecular Transformations, Department of Chemistry and the Institute of Natural Sciences, Nihon University, 3-25-40 Sakurajosui, Setagaya-ku, Tokyo 156-8550, Japan

Abstract

We have developed a first catalytic methodology for the synthesis of primary amides by the catalytic dehydrative amidation ofα- orβ-hydroxycarboxylic acids using inexpensive and safe aqueous ammonia.

Funder

Takahashi Industrial and Economic Research Foundation

Japan Society for the Promotion of Science

Takeda Science Foundation

Ube Foundation

Naohiko Fukuoka Memorial Foundation

Nihon University

Japan Science Society

Pharmaceutical Society of Japan

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2023/CC/D3CC02071A

Reference83 articles.

1. Synthesis of bredinin from 1-.BETA.-D-ribofuranosyl-5-aminoimidazole-4-carboxamide by a photo-reaction.

2. Phthoxazolin, a specific inhibitor of cellulose biosynthesis, produced by a strain of Streptomyces sp.

3. The First Total Synthesis of Natural (−)-Tetracycline

4. Total Synthesis and Stereochemical Revision of the 2-Formylpyrrole Alkaloid Hemerocallisamine I

5. Efficient Transamidation of Primary Carboxamides by in Situ Activation with N,N-Dialkylformamide Dimethyl Acetals

Cited by 2 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Hydroxy-directed peptide bond formation from α-amino acid-derived inert esters enabled by boronic acid catalysis;Chemical Communications;2024

2. Organoboron catalysis for direct amide/peptide bond formation;Chemical Communications;2024