Mechanism of arylboronic acid-catalyzed amidation reaction between carboxylic acids and amines

2013 ◽  
Vol 11 (13) ◽  
pp. 2140 ◽  
Author(s):  
Chen Wang ◽  
Hai-Zhu Yu ◽  
Yao Fu ◽  
Qing-Xiang Guo
Keyword(s):  
Carboxylic Acids ◽  
Arylboronic Acid ◽  
Amidation Reaction ◽  
Acid Catalyzed

Arylboronic Acid Catalyzed Direct Condensation of Carboxylic Acids with Ureas.

ChemInform ◽  
2004 ◽  
Vol 35 (45) ◽  
Author(s):  
Toshikatsu Maki ◽  
Kazuaki Ishihara ◽  
Hisashi Yamamoto
Keyword(s):  
Carboxylic Acids ◽  
Arylboronic Acid ◽  
Acid Catalyzed ◽  
Direct Condensation

Arylboronic Acid-Catalyzed Direct Condensation of Carboxylic Acids with Ureas

Synlett ◽  
2004 ◽  
pp. 1355-1358 ◽  
Author(s):  
Kazuaki Ishihara ◽  
Hisashi Yamamoto ◽  
Toshikatsu Maki
Keyword(s):  
Carboxylic Acids ◽  
Arylboronic Acid ◽  
Acid Catalyzed ◽  
Direct Condensation

Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes

2019 ◽  
Author(s):  
Juha Siitonen ◽  
Padmanabha V. Kattamuri ◽  
Muhammed Yousufuddin ◽  
Laszlo Kurti
Keyword(s):  
Total Synthesis ◽  
Acid Catalysts ◽  
Mechanistic Studies ◽  
Arylboronic Acid ◽  
Synthetic Utility ◽  
Acid Catalyzed

Unprotected keto- and aldoximes are readily <i>C</i>-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly-substituted <i>N</i>-alpha-secondary (2°) and tertiary (3°) hydroxylamines. The method’s synthetic utility is demonstrated with the total synthesis of the trace alkaloid <i>N</i>-methyl-euphococcine. Preliminary experimental and computational mechanistic studies point toward the formation of a boroxine as the active allylating species.<br>

scholarly journals Site-specific Umpolung amidation of carboxylic acids via triplet synergistic catalysis

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yunyun Ning ◽  
Shuaishuai Wang ◽  
Muzi Li ◽  
Jie Han ◽  
Chengjian Zhu ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Amide Bond ◽  
Coupling Reagents ◽  
Complex Molecules ◽  
Bond Forming ◽  
Synergistic Catalysis ◽  
Wide Range ◽  
Amidation Reaction ◽  
Forming Methods

AbstractDevelopment of catalytic amide bond-forming methods is important because they could potentially address the existing limitations of classical methods using superstoichiometric activating reagents. In this paper, we disclose an Umpolung amidation reaction of carboxylic acids with nitroarenes and nitroalkanes enabled by the triplet synergistic catalysis of FeI2, P(V)/P(III) and photoredox catalysis, which avoids the production of byproducts from stoichiometric coupling reagents. A wide range of carboxylic acids, including aliphatic, aromatic and alkenyl acids participate smoothly in such reactions, generating structurally diverse amides in good yields (86 examples, up to 97% yield). This Umpolung amidation strategy opens a method to address challenging regioselectivity issues between nucleophilic functional groups, and complements the functional group compatibility of the classical amidation protocols. The synthetic robustness of the reaction is demonstrated by late-stage modification of complex molecules and gram-scale applications.

scholarly journals A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst

2020 ◽  
Vol 11 (21) ◽  
pp. 5572-5576 ◽  
Author(s):  
Noboru Hayama ◽  
Yusuke Kobayashi ◽  
Eriko Sekimoto ◽  
Anna Miyazaki ◽  
Kiyofumi Inamoto ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Tertiary Amine ◽  
Michael Addition ◽  
Arylboronic Acid ◽  
Unsaturated Carboxylic Acids

An asymmetric thia-Michael addition of arylthiols to α,β-unsaturated carboxylic acids using a thiourea catalyst that bears arylboronic acid and tertiary amine moieties is reported.

Isocarbostyrils. II. The Conversion of 2-Methyl-4-acyl-5-nitroisocarbostyrils to 2-Substituted Indole-4-carboxylic Acids

1971 ◽  
Vol 49 (17) ◽  
pp. 2797-2802 ◽  
Author(s):  
D. E. Horning ◽  
G. Lacasse ◽  
J. M. Muchowski
Keyword(s):  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Alkaline Hydrolysis ◽  
Mannich Reaction ◽  
Reductive Cyclization ◽  
Acid Catalyzed ◽  
Acid Anhydrides ◽  
Hydrolysis Of ◽  
Derivatives Of

The sulfuric acid catalyzed acylation of 2-methyl-5-nitroisocarbostyril with carboxylic acid anhydrides gave the corresponding 4-acylated derivatives 3, which underwent reductive cyclization to 2-substituted derivatives of 4-methyl-1,3,4,5-tetrahydropyrrolo[4.3.2.de]isoquinolin-5-one (4). Alkaline hydrolysis of the six-membered lactam in 4 was accompanied by a retro-Mannich reaction to produce 2-substituted indole-4-carboxylic acids in about 40 % overall yield from 3.

scholarly journals Poly(methylhydrosiloxane) as a green reducing agent in organophosphorus-catalysed amide bond formation

2017 ◽  
Vol 15 (30) ◽  
pp. 6426-6432 ◽  
Author(s):  
Daan F. J. Hamstra ◽  
Danny C. Lenstra ◽  
Tjeu J. Koenders ◽  
Floris P. J. T. Rutjes ◽  
Jasmin Mecinović
Keyword(s):  
Carboxylic Acids ◽  
Phosphine Oxide ◽  
Bond Formation ◽  
Reducing Agent ◽  
Amide Bond ◽  
Amide Bond Formation ◽  
Amidation Reaction

In situ reduction of phosphine oxide by poly(methylhydrosiloxane) leads to efficient amidation reaction between carboxylic acids and amines.

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