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.

Synthesis of Benzamide Derivatives by the Reaction of Arenes and Isocyanides through a C–H Bond Activation Strategy

Synlett ◽  
2017 ◽  
Vol 29 (01) ◽  
pp. 94-98 ◽  
Author(s):  
Mehdi Khalaj ◽  
Mahboubeh Taherkhani ◽  
Seyed Mousavi-Safavi ◽  
Jafar Akbari
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Benzene Derivatives ◽  
Formation Reaction ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Benzamide Derivatives

A carbon–carbon bond formation reaction between isocyanides and benzene derivatives is reported. In contrast to traditional cross-coupling reactions, which require aryl halides or pseudohalides, we use a palladium catalyst to generate the aryl–palladium through C–H bond activation of arenes. This method offers an attractive approach to a range of benzamides from readily accessible benzene derivatives.

Visible light-driven cross-coupling reactions of alkyl halides with phenylacetylene derivatives for C(sp3)–C(sp) bond formation catalyzed by a B12 complex

2019 ◽  
Vol 55 (87) ◽  
pp. 13070-13073 ◽  
Author(s):  
Li Chen ◽  
Yohei Kametani ◽  
Kenji Imamura ◽  
Tsukasa Abe ◽  
Yoshihito Shiota ◽  
...  
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Bond Formation ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Visible Light Driven

Visible light-driven cross-coupling reactions of alkyl halides with phenylacetylene and its derivatives catalyzed by the cobalamin derivative (B12) with the [Ir(dtbbpy)(ppy)2]PF6 photocatalyst at room temperature are reported.

Nickel–glycerol: an efficient, recyclable catalysis system for Suzuki cross coupling reactions using aryl diazonium salts

2016 ◽  
Vol 40 (2) ◽  
pp. 1564-1570 ◽  
Author(s):  
Jeevan Manohar Bhojane ◽  
Sachin Ashok Sarode ◽  
Jayashree Milind Nagarkar
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Environmentally Benign ◽  
Diazonium Salts ◽  
Coupling Reactions ◽  
Formation Reaction ◽  
Cross Coupling Reactions

A palladium free, chemoselective and environmentally benign protocol for a C–C bond formation reaction.

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 Transition-Metal-Free, Visible-Light-Promoted C–S Cross-Coupling through Intermolecular Charge Transfer

Synlett ◽  
2018 ◽  
Vol 29 (19) ◽  
pp. 2449-2455 ◽  
Author(s):  
Garret Miyake ◽  
Bin Liu ◽  
Chern-Hooi Lim
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Materials Science ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Visible Light Driven ◽  
Metal Catalyzed ◽  
Historical Developments

C–S cross-couplings are an important class of reactions ­applied across organic synthesis, materials science, and pharma­ceuticals. Several different methodologies have been developed to achieve this significant transformation. However, currently available synthetic procedures significantly rely on transition metals. This article describes historical developments in the field of transition-metal-catalyzed C–S cross-coupling reactions, the development of a visible-light-driven and catalyst-free approach to C–S bond formation, and future outlooks.

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>

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