Dimsyl Anion Enables Visible‐Light‐Promoted Charge Transfer in Cross‐Coupling Reactions of Aryl Halides

2021 ◽  
Author(s):  
Lei Pan ◽  
Maria Cooke ◽  
Amara Spencer ◽  
Sébastien Laulhé
Keyword(s):  
Charge Transfer ◽  
Visible Light ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

7,10-Dibromo-2,3-dicyanopyrazinophenanthrene Aggregates as a Photosensitizer for Nickel-Catalyzed Aryl Esterification

Synlett ◽  
2021 ◽  
Author(s):  
Xiaoqiang Yu ◽  
Min He ◽  
Shilei Yang ◽  
Ming Bao
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Bond Formation ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Ni Catalyst ◽  
Coupling Reactions ◽  
Formation Reaction ◽  
Cross Coupling Reactions ◽  
Reaction Proceeds

AbstractSelf-assembled aggregates of 7,10-dibromo-2,3-dicyanopyrazinophenanthrene which act as a new organophotocatalyst in combination with Ni catalyst for the Caryl–Oacyl cross-coupling reactions of carboxylic acids with aryl halides are described. This visible-light-induced Caryl–Oacyl bond-formation reaction proceeds smoothly to afford aryl esters with satisfactory to excellent yields.

scholarly journals Polysulfide Anions as Visible Light Photoredox Catalysts for Aryl Cross-Couplings

2020 ◽  
Author(s):  
Haoyu Li ◽  
Xinxin Tang ◽  
Jia Hao Pang ◽  
Xiangyang Wu ◽  
Edwin K. L. Yeow ◽  
...  
Keyword(s):  
Visible Light ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Single Electron ◽  
Coupling Reactions ◽  
Aryl Radicals ◽  
Cross Coupling Reactions ◽  
Redox Couples ◽  
Electron Reduction

Herein, we disclose the use of polysulfide anions as visible light photoredox catalysts for aryl cross-coupling reactions. The reaction design enables single-electron-reduction of aryl halides upon photo-excitation of tetrasulfide dianions (S<sub>4</sub><sup>2–</sup>). The resulting aryl radicals are engaged in (hetero)biaryl cross-coupling, borylation, and hydrogenation in a redox catalytic regime involving S<sub>4</sub><sup>•–</sup>/S<sub>4</sub><sup>2–</sup> and S<sub>3</sub><sup>•–</sup>/S<sub>3</sub><sup>2–</sup> redox couples.

scholarly journals Polysulfide Anions as Visible Light Photoredox Catalysts for Aryl Cross-Couplings

2020 ◽  
Author(s):  
Haoyu Li ◽  
Xinxin Tang ◽  
Jia Hao Pang ◽  
Xiangyang Wu ◽  
Edwin K. L. Yeow ◽  
...  
Keyword(s):  
Visible Light ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Single Electron ◽  
Coupling Reactions ◽  
Aryl Radicals ◽  
Cross Coupling Reactions ◽  
Redox Couples ◽  
Electron Reduction

Herein, we disclose the use of polysulfide anions as visible light photoredox catalysts for aryl cross-coupling reactions. The reaction design enables single-electron-reduction of aryl halides upon photo-excitation of tetrasulfide dianions (S<sub>4</sub><sup>2–</sup>). The resulting aryl radicals are engaged in (hetero)biaryl cross-coupling, borylation, and hydrogenation in a redox catalytic regime involving S<sub>4</sub><sup>•–</sup>/S<sub>4</sub><sup>2–</sup> and S<sub>3</sub><sup>•–</sup>/S<sub>3</sub><sup>2–</sup> redox couples.

Carbon-Heteroatom Cross-Coupling via an Electronically Excited Nickel (II) Complex

2019 ◽  
Author(s):  
Randolph Escobar ◽  
Jeffrey Johannes
Keyword(s):  
Energy Transfer ◽  
Functional Groups ◽  
Cross Coupling ◽  
Reductive Elimination ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
General Methodology ◽  
Cross Coupling Reactions ◽  
Electronically Excited ◽  
Energy Transfer Pathway

<div>While carbon-heteroatom cross coupling reactions have been extensively studied, many methods are specific and</div><div>limited to a set of substrates or functional groups. Reported here is a method that allows for C-O, C-N and C-S cross coupling reactions under one general methodology. We propose that an energy transfer pathway, in which an iridium photosensitizer produces an excited nickel (II) complex, is responsible for the key reductive elimination step that couples aryl halides to 1° and 2° alcohols, anilines, thiophenols, carbamates and sulfonamides.</div>

Water and Sodium Chloride: Essential Ingredients for Robust and Fast Pd‐Catalysed Cross‐Coupling Reactions between Organolithium Reagents and (Hetero)aryl Halides

2019 ◽  
Vol 131 (6) ◽  
pp. 1813-1816 ◽  
Author(s):  
Giuseppe Dilauro ◽  
Andrea Francesca Quivelli ◽  
Paola Vitale ◽  
Vito Capriati ◽  
Filippo Maria Perna
Keyword(s):  
Sodium Chloride ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Organolithium Reagents

scholarly journals Copper’s rapid ascent in visible-light photoredox catalysis

Science ◽  
2019 ◽  
Vol 364 (6439) ◽  
pp. eaav9713 ◽  
Author(s):  
Asik Hossain ◽  
Aditya Bhattacharyya ◽  
Oliver Reiser
Keyword(s):  
Visible Light ◽  
Organic Dyes ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Photoredox Catalysis ◽  
Cross Coupling Reactions ◽  
Rapid Ascent ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Visible-light photoredox catalysis offers a distinct activation mode complementary to thermal transition metal catalyzed reactions. The vast majority of photoredox processes capitalizes on precious metal ruthenium(II) or iridium(III) complexes that serve as single-electron reductants or oxidants in their photoexcited states. As a low-cost alternative, organic dyes are also frequently used but in general suffer from lower photostability. Copper-based photocatalysts are rapidly emerging, offering not only economic and ecological advantages but also otherwise inaccessible inner-sphere mechanisms, which have been successfully applied to challenging transformations. Moreover, the combination of conventional photocatalysts with copper(I) or copper(II) salts has emerged as an efficient dual catalytic system for cross-coupling reactions.

Stereodivergent Hydrosilylation, Hydrostannylation, and Hydrogermylation of α-Trifluoromethylated Alkynes and Their Synthetic Applications

Synthesis ◽  
2016 ◽  
Vol 48 (19) ◽  
pp. 3317-3330 ◽  
Author(s):  
Cédric Tresse ◽  
Stéphane Schweizer ◽  
Philippe Bisseret ◽  
Jacques Lalevée ◽  
Gwilherm Evano ◽  
...  
Keyword(s):  
Functional Group ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

Stereoselective hydrometalation reactions of aryl- and alkyl-substituted trifluoromethylated alkynes with triethylsilane, tributylstannane, and triphenylgermane have been investigated. (E)-α-CF3-Vinylsilanes, -stannanes, and -germanes were obtained under palladium-catalyzed conditions whereas the corresponding (Z)-α-CF3-vinylgermanes were obtained under radical conditions. These reactions proceed in good to excellent yields and possess a broad functional group tolerance. Applications of the (Z)- and (E)-α-CF3-vinylgermanes in palladium-catalyzed cross-coupling reactions with aryl halides having diverse electronic requirements were also investigated. The corresponding (Z)- and (E)-α-CF3-styrenes were obtained as single isomers, thus demonstrating the utility of these versatile synthons for the synthesis of stereodefined trifluoromethylated alkenes.

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