Valorisation of urban waste to access low-cost heterogeneous palladium catalysts for cross-coupling reactions in biomass-derived γ-valerolactone

2021 ◽  
Author(s):  
Federica Valentini ◽  
Francesco Ferlin ◽  
Simone Lilli ◽  
Assunta Marrocchi ◽  
Liu Ping ◽  
...  
Keyword(s):  
Palladium Catalysts ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Urban Waste ◽  
Cross Coupling Reactions ◽  
Simple Protocol

Herein we report a simple protocol for the valorisation of a common urban biowaste.

Dual Nickel/Palladium-Catalyzed Reductive Cross-Coupling Reactions Between Two Phenol Derivatives

2020 ◽  
Author(s):  
Baojian Xiong ◽  
Yue Li ◽  
Yin Wei ◽  
Søren Kramer ◽  
Zhong Lian
Keyword(s):  
Functional Group ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phenol Derivatives ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
One Step ◽  
Aryl Tosylates ◽  
Low Sensitivity

Cross-coupling between substrates that can be easily derived from phenols is highly attractive due to the abundance and low cost of phenols. Here, we report a dual nickel/palladium-catalyzed reductive cross-coupling between aryl tosylates and aryl triflates; both substrates can be accessed in just one step from readily available phenols. The reaction has a broad functional group tolerance and substrate scope (>60 examples). Furthermore, it displays low sensitivity to steric effects demonstrated by the synthesis of a 2,2’disubstituted biaryl and a fully substituted aryl product. The widespread presence of phenols in natural products and pharmaceuticals allow for straightforward late-stage functionalization, illustrated with examples such as Ezetimibe and tyrosine. NMR spectroscopy and DFT calculations indicate that the nickel catalyst is responsible for activating the aryl triflate, while the palladium catalyst preferentially reacts with the aryl tosylate.

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.

scholarly journals Gram-Scale Synthesis of the N-Phenyl Phenothiazine Photocatalyst by Benzyne Addition

2021 ◽  
Author(s):  
Erin Welsh ◽  
Katherine Robertson ◽  
Alex Speed
Keyword(s):  
Transition Metal ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

N-phenyl phenothiazine is one of the most reducing photoredox catalysts. Its synthesis commonly requires transition metal catalyzed cross-coupling reactions. Here we show the syntheses of four aryl phenothiazines via a benzyne route, including a multi-gram scale synthesis of N-phenyl phenothiazine. While yields are modest, the simplicity, low cost, and lack of requirement for cross-coupling catalyst in this synthesis will be attractive to users of this photocatalyst.

scholarly journals Corrigendum: Heterogeneous versus Homogeneous Palladium Catalysts for Cross-Coupling Reactions

ChemCatChem ◽  
2012 ◽  
Vol 4 (8) ◽  
pp. 1030-1030
Author(s):  
Mario Pagliaro ◽  
Valerica Pandarus ◽  
Rosaria Ciriminna ◽  
François Béland ◽  
Piera Demma Carà
Keyword(s):  
Palladium Catalysts ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Heterogeneous versus Homogeneous Palladium Catalysts for Cross-Coupling Reactions

ChemCatChem ◽  
2012 ◽  
Vol 4 (4) ◽  
pp. 432-445 ◽  
Author(s):  
Mario Pagliaro ◽  
Valerica Pandarus ◽  
Rosaria Ciriminna ◽  
François Béland ◽  
Piera Demma Carà
Keyword(s):  
Palladium Catalysts ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

scholarly journals Novel Diketopyrrolopyrrole-Based π-Conjugated Molecules Synthesized Via One-Pot Direct Arylation Reaction

Molecules ◽  
2019 ◽  
Vol 24 (9) ◽  
pp. 1760 ◽  
Author(s):  
Hui Liu ◽  
Xiao-Feng Zhang ◽  
Jing-Zhao Cheng ◽  
Ai-Guo Zhong ◽  
He-Rui Wen ◽  
...  
Keyword(s):  
High Performance ◽  
Electronic Materials ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
One Pot ◽  
Direct Arylation ◽  
Cross Coupling Reactions ◽  
Synthetic Strategy ◽  
Organometallic Precursors

Diketopyrrolopyrrole (DPP) is an important type of π-conjugated building block for high-performance organic electronic materials. DPP-based conjugated materials are usually synthesized via Suzuki, Stille, or Negishi cross-coupling reactions, which require organometallic precursors. In this paper, a series of novel phenyl-cored DPP molecules, including five meta-phenyl-cored molecules and four para-phenyl-cored molecules, have been synthesized in moderate to good yields, in a facile manner, through the Pd-catalyzed direct arylation of C–H bonds, and their optoelectrical properties have been investigated in detail. All new molecules have been fully characterized by NMR, MALDI-TOF MS, elemental analysis, UV–visible spectroscopy, and cyclic voltammetry. This synthetic strategy has evident advantages of atom- and step-economy and low cost, compared with traditional cross-coupling reactions.

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