Photoinduced synthesis of (E)-vinyl sulfones through the insertion of sulfur dioxide

2018 ◽  
Vol 5 (21) ◽  
pp. 3153-3157 ◽  
Author(s):  
Tong Liu ◽  
Yechun Ding ◽  
Xiaona Fan ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Light Irradiation ◽  
Mild Conditions ◽  
Three Component Reaction ◽  
Photoinduced Synthesis

Under visible light irradiation, a three-component reaction of potassium alkyltrifluoroborates, sulfur dioxide and alkynes with the assistance of photocatalysis and in the presence of copper(ii) triflate is described. This transformation affords (E)-vinyl sulfones efficiently with excellent regioselectivity and stereoselectivity under mild conditions.

Synthesis of thiophosphates through a three-component reaction by using sulfur dioxide as the sulfur source

2017 ◽  
Vol 4 (11) ◽  
pp. 2221-2225 ◽  
Author(s):  
Xinxing Gong ◽  
Jiahao Chen ◽  
Jianhe Liu ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Light Irradiation ◽  
Sulfur Source ◽  
Three Component Reaction

Generation of thiophosphates through a three-component reaction of diaryliodonium tetrafluoroborates, 1,4-diazabicyclo[2.2.2]octane-sulfur dioxide (DABCO·(SO2)2), and diarylphosphine oxides under visible light irradiation is described.

Substituted Hantzsch esters as radical reservoirs with the insertion of sulfur dioxide under photoredox catalysis

2019 ◽  
Vol 55 (14) ◽  
pp. 2062-2065 ◽  
Author(s):  
Xuefeng Wang ◽  
Haozhe Li ◽  
Guanyinsheng Qiu ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Light Irradiation ◽  
Photoredox Catalysis ◽  
Three Component Reaction ◽  
Vinyl Azides

A three-component reaction between 4-substituted Hantzsch esters, DABCO·(SO2)2, and vinyl azides in the presence of photoredox catalysts under visible light irradiation is developed. A range of (Z)-2-(alkylsulfonyl)-1-arylethen-1-amines is obtained in moderate to good yields with good regioselectivity and stereoselectivity.

Photoinduced synthesis of alkylalkynyl sulfones through a reaction of potassium alkyltrifluoroborates, sulfur dioxide, and alkynyl bromides

2020 ◽  
Vol 7 (7) ◽  
pp. 938-943 ◽  
Author(s):  
Xinxing Gong ◽  
Min Yang ◽  
Jin-Biao Liu ◽  
Fu-Sheng He ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Light Irradiation ◽  
Sodium Metabisulfite ◽  
Photoinduced Reaction ◽  
Photoinduced Synthesis

A photoinduced reaction of potassium alkyltrifluoroborates, sodium metabisulfite, and alkynyl bromides under visible light irradiation at room temperature is developed.

scholarly journals TiO2 Photocatalyzed C–H Bond Transformation for C–C Coupling Reactions

Catalysts ◽  
2018 ◽  
Vol 8 (9) ◽  
pp. 355 ◽  
Author(s):  
Yi Wang ◽  
Anan Liu ◽  
Dongge Ma ◽  
Shuhong Li ◽  
Chichong Lu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Transition Metal Catalysis ◽  
Light Irradiation ◽  
Coupling Reactions ◽  
Metal Catalysis ◽  
Bond Functionalization ◽  
Tio2 Photocatalysis ◽  
Mild Conditions

Fulfilling the direct inert C–H bond functionalization of raw materials that are earth-abundant and commercially available for the synthesis of diverse targeted organic compounds is very desirable and its implementation would mean a great reduction of the synthetic steps required for substrate prefunctionalization such as halogenation, borylation, and metalation. Successful C–H bond functionalization mainly resorts to homogeneous transition-metal catalysis, albeit sometimes suffering from poor catalyst reusability, nontrivial separation, and severe biotoxicity. TiO2 photocatalysis displays multifaceted advantages, such as strong oxidizing ability, high chemical stability and photostability, excellent reusability, and low biotoxicity. The chemical reactions started and delivered by TiO2 photocatalysts are well known to be widely used in photocatalytic water-splitting, organic pollutant degradation, and dye-sensitized solar cells. Recently, TiO2 photocatalysis has been demonstrated to possess the unanticipated ability to trigger the transformation of inert C–H bonds for C–C, C–N, C–O, and C–X bond formation under ultraviolet light, sunlight, and even visible-light irradiation at room temperature. A few important organic products, traditionally synthesized in harsh reaction conditions and with specially functionalized group substrates, are continuously reported to be realized by TiO2 photocatalysis with simple starting materials under very mild conditions. This prominent advantage—the capability of utilizing cheap and readily available compounds for highly selective synthesis without prefunctionalized reactants such as organic halides, boronates, silanes, etc.—is attributed to the overwhelmingly powerful photo-induced hole reactivity of TiO2 photocatalysis, which does not require an elevated reaction temperature as in conventional transition-metal catalysis. Such a reaction mechanism, under typically mild conditions, is apparently different from traditional transition-metal catalysis and beyond our insights into the driving forces that transform the C–H bond for C–C bond coupling reactions. This review gives a summary of the recent progress of TiO2 photocatalytic C–H bond activation for C–C coupling reactions and discusses some model examples, especially under visible-light irradiation.

An effective photothermal dual-responsive Pd1Cu4/CexOy catalyst for Suzuki–Miyaura coupling reactions under mild conditions

2020 ◽  
Vol 44 (9) ◽  
pp. 3794-3801
Author(s):  
Bo Liu ◽  
Tong Xu ◽  
Chunping Li ◽  
Jie Bai
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Light Irradiation ◽  
Coupling Reactions ◽  
Suzuki Reactions ◽  
Mild Conditions ◽  
Dual Responsive

A Pd1Cu4/CexOy catalyst can efficiently catalyze Suzuki reactions under both heating and visible light irradiation conditions.

An uncommon use of irradiated flavins: Brønsted acid catalysis

2020 ◽  
Vol 56 (42) ◽  
pp. 5661-5664
Author(s):  
Yukihiro Arakawa ◽  
Tomohiro Mihara ◽  
Hiroki Fujii ◽  
Keiji Minagawa ◽  
Yasushi Imada
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Acid Catalysis ◽  
Light Irradiation ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Mild Conditions ◽  
Brönsted Acid ◽  
Bronsted Acid Catalysis

Visible light irradiation to flavins in the presence of thiols and O2 provides Brønsted acidic species that can be used as efficient catalysts for thioacetalizations and for Mannich-type reactions under non-irradiation and mild conditions.

A metal-free route to alkynyl sulfones under photoinduced conditions with the insertion of sulfur dioxide

2020 ◽  
Vol 22 (6) ◽  
pp. 1906-1910 ◽  
Author(s):  
Xinxing Gong ◽  
Min Yang ◽  
Jin-Biao Liu ◽  
Fu-Sheng He ◽  
Xiaona Fan ◽  
...  
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Light Irradiation ◽  
Metal Free

A metal-free route to alkynyl sulfones under photoinduced conditions is accomplished, starting from 4-alkyl Hantzsch esters, sulfur dioxide, and alkynyl bromides under visible light irradiation at room temperature.

A photoinduced reaction of perfluoroalkyl halides with 1,3-diarylprop-2-yn-1-ones catalyzed by DABSO

2017 ◽  
Vol 4 (9) ◽  
pp. 1745-1750 ◽  
Author(s):  
Yuewen Li ◽  
Yiye Lu ◽  
Runyu Mao ◽  
Zhiming Li ◽  
Jie Wu
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Halogen Bond ◽  
Theoretical Calculations ◽  
Light Irradiation ◽  
Efficient Catalyst ◽  
Photoinduced Reaction ◽  
Plausible Mechanism ◽  
Perfluoroalkyl Halides

The sulfur dioxide surrogate of DABCO·(SO2)2 is used as an efficient catalyst for the cleavage of the perfluoroalkyl-halogen bond under visible-light irradiation. A plausible mechanism supported by theoretical calculations is proposed.

Nucleophilic (Radio)Fluorination of Redox-Active Esters via Radical-Polar Crossover Enabled by Photoredox Catalysis

2020 ◽  
Author(s):  
Eric Webb ◽  
John Park ◽  
Erin L. Cole ◽  
David J. Donnelly ◽  
Samuel Bonacorsi, Jr. ◽  
...  
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Light Irradiation ◽  
Active Esters ◽  
Mild Conditions ◽  
Redox Active ◽  
Active Ester ◽  
Electron Transfers ◽  
Ester Substrate ◽  
Nucleophilic Fluorination

<p>We report a redox-neutral method for nucleophilic fluorination of N-hydroxyphthalimide esters using an Ir photocatalyst under visible light irradiation. The method provides access to a broad range of aliphatic fluorides, including primary, secondary, and tertiary benzylic fluorides as well as unactivated tertiary fluorides, that are typically inaccessible by nucleophilic fluorination due to competing elimination. In addition, we show that the decarboxylative fluorination conditions are readily adapted to radiofluorination with [<sup>18</sup>F]KF. We propose that the reactions proceed by two electron transfers between the Ir catalyst and redox-active ester substrate to afford a carbocation intermediate that undergoes subsequent trapping by fluoride. Examples of trapping with O- and C-centered nucleophiles and deoxyfluorination via N-hydroxyphthalimidoyl oxalates are also presented, suggesting that this approach may offer a general blueprint for affecting redox-neutral SN1 substitutions under mild conditions.</p>

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