Fragmentation reactions of protonated α,ω‐diamino carboxylic acids: the importance of functional group interactions

2021 ◽  
Author(s):  
J. Stuart Grossert ◽  
Robert L. White
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Group Interactions ◽  
Fragmentation Reactions

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 Functional Group Selective Derivatization and Gas-Phase Fragmentation Reactions of Plasmalogen Glycerophospholipids

2013 ◽  
Vol 2 (Special_Issue) ◽  
pp. S0015-S0015 ◽  
Author(s):  
Cassie J. Fhaner ◽  
Sichang Liu ◽  
Xiao Zhou ◽  
Gavin E. Reid
Keyword(s):  
Gas Phase ◽  
Functional Group ◽  
Fragmentation Reactions ◽  
Gas Phase Fragmentation

Copper-Catalyzed Decarboxylative N-Arylation of Indole-2-carboxylic Acids

Synthesis ◽  
2019 ◽  
Vol 51 (08) ◽  
pp. 1803-1808 ◽  
Author(s):  
Yan Zhang ◽  
Zhe-Yao Hu ◽  
Xin-Chang Li ◽  
Xun-Xiang Guo
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Aryl Halides ◽  
Synthetic Method ◽  
Alternative Route ◽  
Reaction Proceeds ◽  
High Yields

A novel decarboxylative N-arylation of indole-2-carboxylic acids with aryl halides is developed. The reaction proceeds efficiently in the presence of Cu2O as the catalyst to give the corresponding N-aryl indoles in high yields. This synthetic method shows good functional group tolerance and offers an alternative route to construct N-aryl indoles.

Synthesis of O-Aroyl-N,N-dimethylhydroxylamines through Hypervalent Iodine-Mediated Amination of Carboxylic Acids with N,N-Dimethylformamide

Synthesis ◽  
2017 ◽  
Vol 49 (18) ◽  
pp. 4303-4308 ◽  
Author(s):  
Dong Li ◽  
Chuancheng Zhang ◽  
Qiang Yue ◽  
Zhen Xiao ◽  
Xianglan Wang ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Room Temperature ◽  
Functional Group ◽  
Hypervalent Iodine ◽  
Electrophilic Amination ◽  
Mild Conditions

An efficient protocol for the synthesis of O-aroyl-N,N-dimethylhydroxylamines, which are important electrophilic amination reagents, is described. The reaction between carboxylic acids and N,N-dimethylformamide is mediated by hypervalent iodine and occurs under mild conditions at room temperature to give the desired products in good yields. The process shows good functional group compatibility and air and moisture tolerance.

Copper-catalyzed fluoroalkylation of alkynes, and alkynyl & vinyl carboxylic acids with fluoroalkyl halides

2017 ◽  
Vol 15 (20) ◽  
pp. 4295-4299 ◽  
Author(s):  
Jing-Jing Ma ◽  
Wen-Bin Yi
Keyword(s):  
Carboxylic Acids ◽  
Functional Group

Copper-catalyzed fluoroalkylation of alkynes and alkynyl carboxylic acids has been achieved with high functional-group tolerance and excellent regio- and stereoselectivities.

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