Promoting Highly Diastereoselective γ-C–H Chalcogenation of α-Amino Acids and Aliphatic Carboxylic Acids

ACS Catalysis ◽  
2018 ◽  
Vol 8 (4) ◽  
pp. 2664-2669 ◽  
Author(s):  
Srimanta Guin ◽  
Arghya Deb ◽  
Pravas Dolui ◽  
Souvik Chakraborty ◽  
Vikas Kumar Singh ◽  
...  
Keyword(s):  
Amino Acids ◽  
Carboxylic Acids ◽  
Aliphatic Carboxylic Acids

Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage–Independent Activation of Strong C–O Bonds

2018 ◽  
Author(s):  
Erin Stache ◽  
Alyssa B. Ertel ◽  
Tomislav Rovis ◽  
Abigail G. Doyle
Keyword(s):  
Carboxylic Acids ◽  
Functional Groups ◽  
Single Step ◽  
Direct Access ◽  
Photoredox Catalysis ◽  
Acyl Radical ◽  
Synthetic Strategy ◽  
Acyl Radicals ◽  
Benzyl Radicals ◽  
Aliphatic Carboxylic Acids

Alcohols and carboxylic acids are ubiquitous functional groups found in organic molecules that could serve as radical precursors, but C–O bonds remain difficult to activate. We report a synthetic strategy for direct access to both alkyl and acyl radicals from these ubiquitous functional groups via photoredox catalysis. This method exploits the unique reactivity of phosphoranyl radicals, generated from a polar/SET crossover between a phosphine radical cation and an oxygen centered nucleophile. We first show the desired reactivity in the reduction of benzylic alcohols to the corresponding benzyl radicals with terminal H-atom trapping to afford the deoxygenated product. Using the same method, we demonstrate access to synthetically versatile acyl radicals which enables the reduction of aromatic and aliphatic carboxylic acids to the corresponding aldehydes with exceptional chemoselectivity. This protocol also transforms carboxylic acids to heterocycles and cyclic ketones via intramolecular acyl radical cyclizations to forge new C–O, C–N and C–C bonds in a single step.

Improved QSAR Analysis of the Toxicity of Aliphatic Carboxylic Acids

2003 ◽  
Vol 73 (11) ◽  
pp. 1792-1798 ◽  
Author(s):  
F. P. Maguna ◽  
M. B. Ninez ◽  
N. B. Okulik ◽  
E. A. Castro
Keyword(s):  
Carboxylic Acids ◽  
Qsar Analysis ◽  
Aliphatic Carboxylic Acids

Radical addition to acrylonitrile via catalytic photochemical decarboxylation of aliphatic carboxylic acids

2013 ◽  
Vol 54 (32) ◽  
pp. 4324-4326 ◽  
Author(s):  
Yasuharu Yoshimi ◽  
Sonoka Washida ◽  
Yoshiki Okita ◽  
Keisuke Nishikawa ◽  
Kousuke Maeda ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Radical Addition ◽  
Aliphatic Carboxylic Acids

Syntheses, structures, and properties of multidimensional lithium coordination polymers based on aliphatic carboxylic acids

2013 ◽  
Vol 42 (8) ◽  
pp. 2765-2772 ◽  
Author(s):  
Pei-Chi Cheng ◽  
Wei-Cheng Lin ◽  
Feng-Shuen Tseng ◽  
Ching-Che Kao ◽  
Ting-Guang Chang ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Coordination Polymers ◽  
Structures And Properties ◽  
Aliphatic Carboxylic Acids
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