Visible-light-mediated photoredox minisci C–H alkylation with alkyl boronic acids using molecular oxygen as an oxidant

2020 ◽  
Vol 56 (83) ◽  
pp. 12652-12655 ◽  
Author(s):  
Jianyang Dong ◽  
Fuyang Yue ◽  
Hongjian Song ◽  
Yuxiu Liu ◽  
Qingmin Wang
Keyword(s):  
Visible Light ◽  
Molecular Oxygen ◽  
Boronic Acid ◽  
Room Temperature ◽  
Boronic Acids ◽  
Acid Activation ◽  
Alkylation Reactions

Direct visible-light-mediated Minisci C–H alkylation reactions of N-heteroarenes with alkyl boronic acids at room temperature with molecular oxygen as an oxidant and boronic acid activation reagent were reported.

The Merger of CF3SO2Na and Palladium Catalysis to Enable Decarboxylative Cross-Coupling for the Synthesis of Aromatic Ketones under Room Temperature

2021 ◽  
Author(s):  
Pan Xie ◽  
Cheng Xue ◽  
Cancan Wang ◽  
Dongdong Du ◽  
Sanshan Shi
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Palladium Catalysis ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Aromatic Ketones ◽  
Aryl Ketones ◽  
Oxocarboxylic Acids

A CF3SO2Na/Pd(OAc)2 co-catalyzed strategy is developed to produce aryl ketones via visible-light-induced decarboxylative cross-coupling of α-oxocarboxylic acids and aryl boronic acids. This process was perfomed under air at room temperature,...

scholarly journals Visible-light-mediated Minisci C–H alkylation of heteroarenes with unactivated alkyl halides using O2 as an oxidant

2019 ◽  
Vol 10 (4) ◽  
pp. 976-982 ◽  
Author(s):  
Jianyang Dong ◽  
Xueli Lyu ◽  
Zhen Wang ◽  
Xiaochen Wang ◽  
Hongjian Song ◽  
...  
Keyword(s):  
Visible Light ◽  
Molecular Oxygen ◽  
Room Temperature ◽  
Alkyl Halides

Herein, we report a protocol for direct visible-light-mediated Minisci C–H alkylation of heteroarenes with unactivated alkyl halides using molecular oxygen as an oxidant at room temperature.

Visible light-promoted copper catalyzed regioselective acetamidation of terminal alkynes by arylamines

2020 ◽  
Vol 22 (4) ◽  
pp. 1164-1170 ◽  
Author(s):  
V. Kishore Kumar Pampana ◽  
Arunachalam Sagadevan ◽  
Ayyakkannu Ragupathi ◽  
Kuo Chu Hwang
Keyword(s):  
Visible Light ◽  
Molecular Oxygen ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Light Irradiation ◽  
Terminal Alkynes

Herein, we describe a copper photoredox catalyzed synthesis of acetamide via regioselective C–N coupling of arylamines with terminal alkynes using molecular oxygen (O2) as an oxidant at room temperature under visible light irradiation (47 examples).

scholarly journals Using Visible Light to Continuously Tune Boronic Acid–ester Equilibria

2020 ◽  
Author(s):  
Joseph Accardo ◽  
Emily McClure ◽  
Martin Mosquera ◽  
Julia Kalow
Keyword(s):  
Visible Light ◽  
Boronic Acid ◽  
Red Light ◽  
Binding Constants ◽  
Boronic Acids ◽  
Star Polymer ◽  
Light Competition ◽  
Biologically Relevant ◽  
Boronic Esters ◽  
Poly Ethylene

<p>We report a series of azobenzene boronic acids that can be used to control diol binding via photochemical isomerization. When the boronic acid is <i>ortho</i> to the azo group, the thermodynamically-favored <i>E</i> isomer binds weakly with diols to form boronic esters. Isomerization of the <i>E</i> azobenzene to its <i>Z</i> isomer enhances diol binding, and the extent of this enhancement is affected by the azobenzene structure. 2,6-Dimethoxy azobenzene boronic acids show over 20-fold enhancement in binding upon <i>E</i>–<i>Z</i> isomerization, which can be triggered with red light. Competition experiments and computational studies suggest that the changes in binding affinity originate from stabilization of the <i>E</i> boronic acids and destabilization of the <i>E</i> boronic esters. We demonstrate a correlation between diol binding and photostationary state: different wavelengths of irradiation yield different quantities of bound diol. Higher binding constants for the <i>Z</i> isomer relative to the <i>E</i> isomer was observed with all diols investigated, including cyclic diols, nitrocatechol, biologically relevant drugs, and polyols. This photoswitch was employed to “catch and release” a fluorescently tagged diol in buffered water. By tethering this photoswitch to a poly(ethylene glycol) star polymer, we can tune the stiffness of covalent adaptable hydrogels using different wavelengths of visible light. This work establishes photoswitchable equilibria as a tool for the reversible ligation of molecular and macromolecular species.</p>

scholarly journals Using Visible Light to Tune Boronic Acid–ester Equilibria

2020 ◽  
Author(s):  
Joseph Accardo ◽  
Emily McClure ◽  
Martin Mosquera ◽  
Julia Kalow
Keyword(s):  
Visible Light ◽  
Boronic Acid ◽  
Red Light ◽  
Binding Constants ◽  
Boronic Acids ◽  
Star Polymer ◽  
Light Competition ◽  
Biologically Relevant ◽  
Boronic Esters ◽  
Poly Ethylene

<p>We report a series of azobenzene boronic acids that reversibly control the extent of diol binding via photochemical isomerization. When the boronic acid is <i>ortho</i> to the azo group, the thermodynamically-favored <i>E</i> isomer binds weakly with diols to form boronic esters. Isomerization of the <i>E</i> azobenzene to its <i>Z</i> isomer enhances diol binding, and the magnitude of this enhancement is affected by the azobenzene structure. 2,6-Dimethoxy azobenzene boronic acids show over 20-fold enhancement in binding upon <i>E–Z</i> isomerization, which can be triggered with red light. Competition experiments and computational studies suggest that the changes in binding affinity originate from stabilization of the <i>E</i> boronic acids and destabilization of the <i>E</i> boronic esters. We demonstrate a correlation between diol binding and photostationary state: different wavelengths of irradiation yield different quantities of bound diol. Higher binding constants for the <i>Z</i> isomer relative to the <i>E</i> isomer was observed with all diols investigated, including cyclic diols, nitrocatechol, biologically relevant compounds, and polyols. This photoswitch was employed to “catch and release” a fluorescently tagged diol in buffered water. By tethering this photoswitch to a poly(ethylene glycol) star polymer, we can tune the stiffness of covalent adaptable hydrogels using different wavelengths of visible light. This work establishes photoswitchable equilibria as a tool for the reversible ligation of molecular and macromolecular species.</p>

Recyclable Cu@C3N4-Catalyzed Hydroxylation of Aryl Boronic Acids in Water under Visible Light: Synthesis of Phenols under Ambient Conditions and Room Temperature

2020 ◽  
Vol 8 (7) ◽  
pp. 2682-2687 ◽  
Author(s):  
Mehwish Hussain Muhammad ◽  
Xiao-Lan Chen ◽  
Yan Liu ◽  
Tao Shi ◽  
Yuyu Peng ◽  
...  
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Boronic Acids ◽  
Ambient Conditions

Visible-light-mediated minisci C–H alkylation of heteroarenes with 4-alkyl-1,4-dihydropyridines using O2 as an oxidant

2020 ◽  
Vol 22 (17) ◽  
pp. 5599-5604
Author(s):  
Jianyang Dong ◽  
Fuyang Yue ◽  
Wentao Xu ◽  
Hongjian Song ◽  
Yuxiu Liu ◽  
...  
Keyword(s):  
Visible Light ◽  
Molecular Oxygen ◽  
Room Temperature

Minisci C–H alkylation of N-heteroarenes with 4-alkyl-1,4-dihydropyridines at room temperature with molecular oxygen as an oxidant was developed.

Visible light-induced aerobic oxidation of diarylalkynes to α-diketones catalyzed by copper-superoxo at room temperature

2020 ◽  
Vol 22 (14) ◽  
pp. 4426-4432 ◽  
Author(s):  
Vaibhav Pramod Charpe ◽  
Arunachalam Sagadevan ◽  
Kuo Chu Hwang
Keyword(s):  
Visible Light ◽  
Molecular Oxygen ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Aerobic Oxidation ◽  
Low Energy ◽  
Light Irradiation ◽  
Environmentally Benign ◽  
Chloride Salt ◽  
Feasible Method

We demonstrate an environmentally benign and economically feasible method for the oxidation of stable diarylalkynes to diketones at room temperature using the inexpensive copper(ii) chloride salt and molecular oxygen under low energy visible light irradiation.

scholarly journals Using Visible Light to Tune Boronic Acid–ester Equilibria

2020 ◽  
Author(s):  
Joseph Accardo ◽  
Emily McClure ◽  
Martin Mosquera ◽  
Julia Kalow
Keyword(s):  
Visible Light ◽  
Boronic Acid ◽  
Red Light ◽  
Binding Constants ◽  
Boronic Acids ◽  
Star Polymer ◽  
Light Competition ◽  
Biologically Relevant ◽  
Boronic Esters ◽  
Poly Ethylene

<p>We report a series of azobenzene boronic acids that reversibly control the extent of diol binding via photochemical isomerization. When the boronic acid is <i>ortho</i> to the azo group, the thermodynamically-favored <i>E</i> isomer binds weakly with diols to form boronic esters. Isomerization of the <i>E</i> azobenzene to its <i>Z</i> isomer enhances diol binding, and the magnitude of this enhancement is affected by the azobenzene structure. 2,6-Dimethoxy azobenzene boronic acids show over 20-fold enhancement in binding upon <i>E–Z</i> isomerization, which can be triggered with red light. Competition experiments and computational studies suggest that the changes in binding affinity originate from stabilization of the <i>E</i> boronic acids and destabilization of the <i>E</i> boronic esters. We demonstrate a correlation between diol binding and photostationary state: different wavelengths of irradiation yield different quantities of bound diol. Higher binding constants for the <i>Z</i> isomer relative to the <i>E</i> isomer was observed with all diols investigated, including cyclic diols, nitrocatechol, biologically relevant compounds, and polyols. This photoswitch was employed to “catch and release” a fluorescently tagged diol in buffered water. By tethering this photoswitch to a poly(ethylene glycol) star polymer, we can tune the stiffness of covalent adaptable hydrogels using different wavelengths of visible light. This work establishes photoswitchable equilibria as a tool for the reversible ligation of molecular and macromolecular species.</p>

Efficient photocatalytic oxygenation of alkenes by water soluble sensitizer in organic–water biphasic media

2016 ◽  
Vol 20 (06) ◽  
pp. 670-676 ◽  
Author(s):  
Mahdi Hajimohammadi ◽  
Hoda Ghasemi
Keyword(s):  
Methylene Blue ◽  
Visible Light ◽  
Singlet Oxygen ◽  
Molecular Oxygen ◽  
Rose Bengal ◽  
Room Temperature ◽  
Water Soluble ◽  
Oxygen Production ◽  
Oxidation Of Olefins ◽  
Major Route

A new green, environmentally and economically photooxygenation of olefins by molecular oxygen in the presence of 4-carboxyl tetra phenyl porphyrin (H2TCPP), Rose Bengal (RB), Methylene Blue (MB) and some metallosensitizers (MS) such as cobalt phthalocyaninesulfonate (Coph(SO3H)[Formula: see text], MnTCPPCl, FeTCPPCl and SbTPP(OH)2 as water–soluble sensitizers in organic–water biphasic media at room temperature under visible light was illustrated. The products were obtained with 100% conversion by H2TCPP and 100% selectivity by Coph(SO3H)4. Also in this study, singlet oxygen production as the major route for oxidation of olefins was proved.

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