Visible-light photocatalytic oxidation of 1,3-dicarbonyl compounds and carbon–carbon bond formation

2014 ◽  
Vol 1 (5) ◽  
pp. 551 ◽  
Author(s):  
Marion Daniel ◽  
Louis Fensterbank ◽  
Jean-Philippe Goddard ◽  
Cyril Ollivier
Keyword(s):  
Visible Light ◽  
Photocatalytic Oxidation ◽  
Bond Formation ◽  
Dicarbonyl Compounds ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Visible Light Photocatalytic

scholarly journals Metal-free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide C–H activation

2019 ◽  
Vol 10 (6) ◽  
pp. 1687-1691 ◽  
Author(s):  
Mrinmoy Das ◽  
Minh Duy Vu ◽  
Qi Zhang ◽  
Xue-Wei Liu
Keyword(s):  
Visible Light ◽  
Bond Formation ◽  
Formation Processes ◽  
New Approach ◽  
Carbon Bond ◽  
Metal Free ◽  
Carbon Carbon Bond ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
New Strategy

Phosphonium ylides have shown their synthetic usefulness in important carbon–carbon bond formation processes. Our new strategy employs phosphonium ylides as novel carbyne equivalents and features a new approach for constructing carbon–carbon bonds from alkenes.

Palladium chloride catalyzed photochemical Heck reaction

2013 ◽  
Vol 91 (5) ◽  
pp. 348-351 ◽  
Author(s):  
Suresh B. Waghmode ◽  
Sudhir S. Arbuj ◽  
Bina N. Wani ◽  
C.S. Gopinath
Keyword(s):  
Visible Light ◽  
Heck Reaction ◽  
Palladium Nanoparticles ◽  
Bond Formation ◽  
Aryl Halides ◽  
Palladium Chloride ◽  
Carbon Bond ◽  
Excellent Yield ◽  
Carbon Carbon Bond ◽  
Uv Visible

PdCl2 catalyzed carbon–carbon bond formation (Heck reaction) between substituted aryl halides and olefins was carried out without a ligand, under irradiation with UV–visible light. The results demonstrated that UV–visible light accelerated the rate of the reaction, leading to an excellent yield of corresponding products. The recovered palladium nanoparticles could be thermally recycled several times. PdCl2 gave excellent conversion up to the fifth addition of substrate.

Visible light-driven selective carbon–carbon bond formation for the production of vicinal diols

2020 ◽  
Vol 4 (11) ◽  
pp. 5488-5492
Author(s):  
Peng Bai ◽  
Xinli Tong ◽  
Yiqi Gao ◽  
Song Xue
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Bond Formation ◽  
Light Irradiation ◽  
Carbon Bond ◽  
Benzylic Alcohols ◽  
Radical Coupling ◽  
Carbon Carbon Bond ◽  
Visible Light Driven ◽  
Vicinal Diols

A green and sustainable production of vicinal diols via the photocatalytic radical coupling of benzylic alcohols has been developed under visible light irradiation.

Organolead(IV) Tricarboxylates, New Reagents for Organic Synthesis

1991 ◽  
Vol 44 (10) ◽  
pp. 1353 ◽  
Author(s):  
JT Pinhey
Keyword(s):  
Organic Synthesis ◽  
Bond Formation ◽  
Dicarbonyl Compounds ◽  
Carbon Bond ◽  
Carbon Nucleophiles ◽  
Carbon Carbon Bond ◽  
Marked Preference ◽  
Soft Carbon

Aryl-, vinyl- and alk-1-ynyl-lead(IV) tricarboxylates act as electrophilic arylating, vinylating and alkynylating agents, respectively, with a variety of nucleophiles, especially soft carbon nucleophiles such as β- dicarbonyl compounds, phenols and nitroalkanes. In their reactions, they show a marked preference for carbon-carbon bond formation, especially in which a quaternary centre is produced. The formation and the synthetically useful reactions of these new reagents are reviewed.

scholarly journals Visible light-induced reduction system of diphenylviologen derivative with water-soluble porphyrin for biocatalytic carbon–carbon bond formation from CO2

2018 ◽  
Vol 90 (11) ◽  
pp. 1723-1733 ◽  
Author(s):  
Takayuki Katagiri ◽  
Kohei Fujita ◽  
Shusaku Ikeyama ◽  
Yutaka Amao
Keyword(s):  
Steady State ◽  
Visible Light ◽  
Bond Formation ◽  
Redox System ◽  
Water Soluble ◽  
Reduced Form ◽  
Electron Mediator ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Water Soluble Porphyrin

Abstract From the view point of green chemistry, CO2 utilization technologies with solar energy including the photoredox system have been received a lot of attention. As one of them, photoredox system containing a photosensitizer and a catalyst catalyzing a reaction of a carbon–carbon bond formation from CO2 as a feed stock were constructed. In a recent study, we reported the visible light-induced malate (C4 compound) production from pyruvate (C3 compound) and CO2 due to carbon–carbon bond formation with the system consisting an electron donor, a photosensitizer, diphenylviologen (PV2+) derivative as an electron mediator in the presence of malic enzyme (ME). However, the interaction between a photosensitizer and PV2+ derivative has not been clarified yet. In this study, water-soluble PV2+ derivative, 1,1′-bis(p-sulfonatophenyl)-4,4′-bipyridinium salt (PSV2+) was synthesized, and its electro-, photochemical properties were evaluated. Moreover, the photoredox properties of PSV2+ with water-soluble Zn porphyrin were studied using fluorescence spectroscopy and steady state irradiation. The fluorescence of Zn porphyrin was quenched by PSV2+ and the two-electron reduced form of PSV2+ were produced with Zn porphyrin with steady state irradiation. In addition, reaction solution containing triethanolamine, tetraphenylporphyrin tetrasulfonate, pyruvate, ME, Mg2+ and PSV2+ in CO2 saturated bis-tris buffer (pH 7.4) was irradiated with visible light, the oxaloacetate and malate were produced. This result indicates that PSV2+ is an efficient electron mediator in the visible light-induced redox system for carbon–carbon bond formation with ME from CO2 as a feedstock.

ChemInform Abstract: Rhenium- and Manganese-Catalyzed Carbon-Carbon Bond Formation Using 1,3-Dicarbonyl Compounds and Alkynes

ChemInform ◽  
2011 ◽  
Vol 42 (23) ◽  
pp. no-no
Author(s):  
Yoichiro Kuninobu ◽  
Atsushi Kawata ◽  
Salprima S. Yudha ◽  
Hisatsugu Takata ◽  
Mitsumi Nishi ◽  
...  
Keyword(s):  
Bond Formation ◽  
Dicarbonyl Compounds ◽  
Carbon Bond ◽  
Carbon Carbon Bond

Development of a dye molecule-biocatalyst hybrid system with visible-light induced carbon–carbon bond formation from CO2 as a feedstock

2017 ◽  
Vol 198 ◽  
pp. 73-81 ◽  
Author(s):  
Yutaka Amao ◽  
Shusaku Ikeyama ◽  
Takayuki Katagiri ◽  
Kohei Fujita
Keyword(s):  
Visible Light ◽  
Electron Donor ◽  
Pyruvic Acid ◽  
Malic Acid ◽  
Bond Formation ◽  
Major Product ◽  
Water Soluble ◽  
Electron Mediator ◽  
Carbon Bond ◽  
Carbon Carbon Bond

Recently, CO2 utilization technology, including artificial photosynthesis, has received much attention. In this field, CO2 is used as a feedstock for fuels, polymers and in other chemical processes. Of note are malic enzymes (MEs) which catalyze the reaction of malic acid to pyruvic acid and CO2 with the co-enzyme NADP+, and catalyze the reverse reaction of pyruvic acid and CO2 to malic acid with the co-enzyme NADPH. Thus, MEs are also an attractive biocatalyst for carbon–carbon bond formation from CO2. Studies of the visible light-induced malic acid production from pyruvic acid and CO2 using an electron donor, a photosensitizer, an electron mediator, ferredoxin-NADP+ reductase, NADP+, and ME have been reported. However, modification of these systems is required, as they are very complicated. In this study, the visible light-induced carbon–carbon bond formation from pyruvic acid and CO2 with ME using the photoreduction of 1,1′-diphenyl-4,4′-bipyridinium salt derivatives as a novel electron mediator with water-soluble tetraphenylporphyrin tetrasulfonate (H2TPPS) in the presence of triethanolamine (TEOA) as an electron donor was developed. When a sample solution containing TEOA, H2TPPS, 1,1′-diphenyl-4,4′-bipyridinium salt derivative, pyruvic acid, and ME in CO2-saturated bis–tris buffer was irradiated, the major product was oxaloacetic acid. Thus, a visible light-induced photoredox system for carbon–carbon bond formation from CO2 with ME using 1,1′-diphenyl-4,4′-bipyridinium salt derivative as an electron mediator was developed.

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