Iridium(III)-Catalyzed Direct Intermolecular Chemoselective α-Amidation of Masked Aliphatic Carboxylic Acids with Dioxazolones via Nitrene Transfer

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

Russian Journal of General Chemistry ◽

10.1023/b:rugc.0000018657.40304.45 ◽

2003 ◽

Vol 73 (11) ◽

pp. 1792-1798 ◽

Cited By ~ 7

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

Tetrahedron Letters ◽

10.1016/j.tetlet.2013.06.020 ◽

2013 ◽

Vol 54 (32) ◽

pp. 4324-4326 ◽

Cited By ~ 21

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

Dalton Transactions ◽

10.1039/c2dt32424e ◽

2013 ◽

Vol 42 (8) ◽

pp. 2765-2772 ◽

Cited By ~ 14

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

Thermal conductivity and viscosity of normal C2-C6 aliphatic carboxylic Acids

Journal of Applied Chemistry and Biotechnology ◽

10.1002/jctb.5020270144 ◽

2007 ◽

Vol 27 (1) ◽

pp. 296-302 ◽

Cited By ~ 7

Author(s):

Walter Kynaston ◽

John F. Martin

Keyword(s):

Thermal Conductivity ◽

Carboxylic Acids ◽

Aliphatic Carboxylic Acids

Silver-Mediated C−S Cross-Coupling of Di(pyrimidin-2-yl) Disulfides with Aliphatic Carboxylic Acids

ChemistrySelect ◽

10.1002/slct.201601870 ◽

2017 ◽

Vol 2 (3) ◽

pp. 1140-1143 ◽

Cited By ~ 3

Author(s):

Wen-Juan Wang ◽

Xiao-Jun Liu ◽

Xi-Cun Wang

Keyword(s):

Carboxylic Acids ◽

Cross Coupling ◽

Aliphatic Carboxylic Acids

ChemInform Abstract: Silver-Catalyzed Decarboxylative Trifluoromethylthiolation of Aliphatic Carboxylic Acids in Aqueous Emulsion.

ChemInform ◽

10.1002/chin.201449056 ◽

2014 ◽

Vol 45 (49) ◽

pp. no-no

Author(s):

Feng Hu ◽

Xinxin Shao ◽

Dianhu Zhu ◽

Long Lu ◽

Qilong Shen

Keyword(s):

Carboxylic Acids ◽

Aqueous Emulsion ◽

Aliphatic Carboxylic Acids

Intercalation of aliphatic carboxylic acids into layered structures of vanadyl sulfate, phosphate and arsenate

Inorganica Chimica Acta ◽

10.1016/s0020-1693(00)84852-5 ◽

1990 ◽

Vol 176 (2) ◽

pp. 255-259 ◽

Cited By ~ 23

Author(s):

L. Benš ◽

J. Votinský ◽

J. Kalousová ◽

K. Handlíř

Keyword(s):

Carboxylic Acids ◽

Layered Structures ◽

Vanadyl Sulfate ◽

Aliphatic Carboxylic Acids

QSTR mathematical models for the toxicity of aliphatic carboxylic acids on tetrahymena pyriformis

Creative Mathematics and Informatics ◽

10.37193/cmi.2013.02.09 ◽

2013 ◽

Vol 22 (2) ◽

Author(s):

Zoița Mărioara Berinde

Keyword(s):

Dissociation Constant ◽

Carboxylic Acids ◽

Aquatic Toxicity ◽

Tetrahymena Pyriformis ◽

Refraction Index ◽

Linear Regression Models ◽

Acidic Dissociation ◽

Growth Assay ◽

Aliphatic Carboxylic Acids ◽

Acidic Dissociation Constant

The present work represents an attempt to improve QSTR models for aquatic toxicity of 3838 aliphatic carboxylic acids tested in the Tetrahymena pyriformis population growth assay, using the topological index ZEP and the following nine main electrotopological and molecular descriptors: acidic dissociation constant, 1-octanol/water partition coefficient, the energy of the lowest unoccupied molecular orbital, acidic dissociation constant, molar refractivity, refraction index, surface tension, polarizability and, electrotopological states. Several different relations between toxicity [loglog(IGC50-1)] and the molecular and topological properties were examined, and a group of multiple linear regression models with high fitness scores were generated.