Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Copper(ii)-photocatalyzed decarboxylative oxygenation of carboxylic acids

Journal Article · · ChemComm
DOI:https://doi.org/10.1039/d2cc00570k· OSTI ID:1863588
Showcasing the concept of light-induced homolysis for the generation of radicals, the CuII-photocatalyzed decarboxylative oxygenation of carboxylic acids with molecular oxygen as the terminal oxidant is described. Here, two CuII-carboxylate complexes with different coordination geometries were synthesized and characterized by X-ray analysis, correlating their structure with their ability to initiate light-induced decarboxylations.
Research Organization:
North Carolina State Univ., Raleigh, NC (United States)
Sponsoring Organization:
USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
SC0019370
OSTI ID:
1863588
Alternate ID(s):
OSTI ID: 1846330
Journal Information:
ChemComm, Journal Name: ChemComm Journal Issue: 28 Vol. 58; ISSN 1359-7345
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

References (23)

Visible-Light Photocatalysis: Does It Make a Difference in Organic Synthesis? journal June 2018
Decarboxylative Benzylation of Aryl and Alkenyl Boronic Esters journal March 2018
Visible‐Light‐Accelerated Copper(II)‐Catalyzed Regio‐ and Chemoselective Oxo‐Azidation of Vinyl Arenes journal July 2018
Visible‐Light‐Induced Homolysis of Earth‐Abundant Metal‐Substrate Complexes: A Complementary Activation Strategy in Photoredox Catalysis journal June 2021
Decarboxylation as the Key Step in C−C Bond-Forming Reactions journal February 2017
Speciation Behavior of Copper(II) Acetate in Simple Organic Solvents – Revealing the Effect of Trace Water journal February 2014
Three dinuclear copper(II) carboxylates with the paddle-wheel cage structure as intermediates in copper(II) catalyzed oxidations of carboxylic acids. X-ray crystal structures of [tetrakis(diphenyl acetato-μ-O,O′)bis(acetonitrile-N)dicopper(II)] tetrakis(acetonitrile), [] and [tetrakis(1-phenyl-1-carboxylato-μ-O,O′-cyclopentane)-bis(ethanol-O)dicopper(II)] bis (ethanol) journal January 1998
Visible Light-Driven, Copper-Catalyzed Aerobic Oxidative Cleavage of Cycloalkanones journal June 2021
Photoredox Catalysis in Organic Chemistry journal June 2016
Direct Evidence of Visible Light-Induced Homolysis in Chlorobis(2,9-dimethyl-1,10-phenanthroline)copper(II) journal June 2020
Dinuclear Paddle-Wheel Copper(II) Carboxylates in the Catalytic Oxidation of Carboxylic Acids. Unusual Polymeric Chains Found in the Single-Crystal X-ray Structures of [Tetrakis(μ-1-phenylcyclopropane-1-carboxylato- O , O‘ )bis(ethanol- O )dicopper(II)] and catena -Poly[[bis(μ-diphenylacetato- O : O‘ )dicopper](μ 3 -diphenylacetato-1- O :2- O‘ :1‘- O‘ )(μ 3 -diphenylacetato-1- O :2- O‘ :2‘- O‘ )] journal September 1997
Photochemistry of copper complexes. Copper(II) malonate system journal February 1975
Orbital interactions in metal dimer complexes journal August 1975
Photolyses of Metal Compounds: Cupric Chloride in Organic Media journal June 1962
Radical Decarboxylative Carbometalation of Benzoic Acids: A Solution to Aromatic Decarboxylative Fluorination journal April 2021
Photoactive Complexes with Earth-Abundant Metals journal September 2018
Copper(II)-Catalyzed Asymmetric Photoredox Reactions: Enantioselective Alkylation of Imines Driven by Visible Light journal October 2018
Aldehydes and Ketones Formation: Copper-Catalyzed Aerobic Oxidative Decarboxylation of Phenylacetic Acids and α-Hydroxyphenylacetic Acids journal February 2014
Decarboxylative cross-nucleophile coupling via ligand-to-metal charge transfer photoexcitation of Cu(ii) carboxylates journal January 2022
Magneto-structural versatility of copper( ii )-3-phenylpropionate coordination polymers with N-donor coligands journal January 2016
Decarboxylative coupling reactions: a modern strategy for C–C-bond formation journal January 2011
Mechanism of O 2 activation and substrate hydroxylation in noncoupled binuclear copper monooxygenases journal October 2016
Copper’s rapid ascent in visible-light photoredox catalysis journal May 2019