The story of C-C bond formation includes several reactions, and surely Suzuki-Miyaura is among the most outstanding ones. Herein, a brief historical overview of insights regarding the reaction mechanism is provided. In particular, the formation of the catalytically active species is probably the main concern, thus the preactivation is in competition with, or even assumes the role of the rate determining step (rds) of the overall reaction. Computational chemistry is key in identifying the rds and thus leading to milder conditions on an experimental level by means of predictive catalysis.

Mechanistic Aspects of the Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction.

Dipolar aprotic and ethereal solvents comprise just over 40% of all organic solvents utilized in synthetic organic, medicinal, and process chemistry. Unfortunately, many of the common “go-to” solvents are considered to be “less-preferable” for a number of environmental, health, and safety (EHS) reasons such as toxicity, mutagenicity, carcinogenicity, or for practical handling reasons such as flammability and volatility. Recent legislative changes have initiated the implementation of restrictions on the use of many of the commonly employed dipolar aprotic solvents such as dimethylformamide (DMF) and N-methyl-2-pyrrolidinone (NMP), and for ethers such as 1,4-dioxane. Thus, with growing legislative, EHS, and societal pressures, the need to identify and implement the use of alternative solvents that are greener, safer, and more sustainable has never been greater. Within this review, the ubiquitous nature of dipolar aprotic and ethereal solvents is discussed with respect to the physicochemical properties that have made them so appealing to synthetic chemists. An overview of the current legislative restrictions being imposed on the use of dipolar aprotic and ethereal solvents is discussed. A variety of alternative, safer, and more sustainable solvents that have garnered attention over the past decade are then examined, and case studies and examples where less-preferable solvents have been successfully replaced with a safer and more sustainable alternative are highlighted. Finally, a general overview and guidance for solvent selection and replacement are included in the Supporting Information of this review.

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

Photocatalytic degradation by TiO2-conjugated/coordination polymer heterojunction: Preparation, mechanisms, and prospects

The challenging transamidation of unactivated tertiary amides has been accomplished via cooperative acid/iodide catalysis. Most crucially, the method provides a novel manifold to re-route the reactivity of unactivated N,N-dialkyl amides through reactive acyl iodide intermediates, thus reverting the classical order of reactivity of carboxylic acid derivatives. This method provides a direct route to amide-to-amide bond interconversion with excellent chemoselectivity using equivalent amounts of amines. The combination of acid and iodide has been identified as the essential factor to activate the amide C-N bond through electrophilic catalytic activation, enabling the production of new desired transamidated products with wide substrate scope of both unactivated amides and amines, including late-stage functionalization of complex APIs (>80 examples). We anticipate that this powerful activation mode of unactivated amide bonds will find broad-ranging applications in chemical synthesis.

https://rss.onlinelibrary.wiley.com/doi/am-pdf/10.1002/anie.202202794

Highly Chemoselective Transamidation of Unactivated Tertiary Amides by Electrophilic N-C(O) Activation via Amide-to-Acyl Iodide Re-Routing.

In this study, a novel silver [email protected] imidazolate framework-8 (Ag3PO4@ZIF-8) p-n heterojunction was fabricated at room temperature using the chemical precipitation method. The photocatalytic properties of the developed p-n heterojunction were investigated with respect to organic water pollutants. The effects of the operation parameters on the photocatalytic performance of the fabricated photocatalyst were also studied. The fabricated Ag3PO4@ZIF-8 p-n heterojunction exhibited excellent photocatalytic properties with respect to organic pollutants crystal violet (CV), Congo red (CR), and rhodamine B (Rh B). The total organic carbon (TOC) measurements revealed that the developed Ag3PO4@ZIF-8 p-n heterojunction mineralized 99.0% of Rh B, 90.7% of CV, and 94.7% of CR in 120 min. The heterojunction also exhibited excellent cyclic stability, which is crucial for practical applications. The excellent photocatalytic performance of the developed Ag3PO4@ZIF-8 p-n heterojunction could be ascribed to the suppression of the photogenerated charge recombination, enhancement of the surface area, p-n heterojunction formation, and extended light absorption. Therefore, the developed heterojunction is promising for environmental remediation in general, and for photocatalysis-based treatment of organic pollutant-containing wastewater in particular. 

Novel Ag3PO4@ZIF-8 p-n heterojunction for effective photodegradation of organic pollutants

A range of environmentally friendly solvents was evaluated in the Suzuki–Miyaura coupling of amides in an attempt to provide the first solvent selection guide for the powerful C–C coupling by amide...

Green Solvent Selection for Suzuki–Miyaura Coupling of Amides

Green-Solvent Selection for Acyl Buchwald–Hartwig Cross-Coupling of Amides (Transamidation)

Non-food bioactive products: Diversified invention of 1,2,4-oxadiazole-containing amide derivatives for novel fungicidal candidate discovery

Construction of a Hollow Bioi/Tio2/Zif-8 Heterojunction: Enhanced Photocatalytic Performance for Norfloxacin Degradation and Mechanistic Insight

As a continuous effort toward developing novel and highly efficient agrochemicals for integrated management of crop pathogens, two series of oxime ester derivatives from indole and tetrahydroquinoline natural scaffolds were prepared. Guided by the preliminary inhibition rates against ubiquitous and representative fungi, the antifungal profile of the target compounds against Valsa mali was intensively and extensively studied. The tetrahydroquinoline-based derivatives 12a-12r exerted a promising inhibition effect, especially against V. mali. The remarkable compounds 12p (R = 4-OCF3) and 12r (R = 4-OBn) with EC50 values of 0.81 and 0.47 μg/mL, respectively, have a far more prominent activity than commercial fungicide trifloxystrobin. The biochemistry and physiology responses of V. mali after treatment with target compound 12p was examined, and the fruit body production, hyphae morphology, and organelles were profoundly affected. Moreover, the curative effects of compound 12p on apple detached branches and leaves were 57.69 and 64.84% at 100 μg/mL, respectively, which were even superior to that of trifloxystrobin. Meanwhile, the three-dimensional quantitative structure-activity relationship model [comparative molecular field analysis (CoMFA): q2 = 0.823, r2 = 0.924, F = 189.781, and standard error of estimation (SEE) = 0.138 and comparative molecular similarity index analysis (CoMSIA): q2 = 0.795, r2 = 0.904, F = 145.644, and SEE = 0.156] indicated that the antifungal activity of target compounds was facilitated by crucial structural factors, which would render inspiration for further design and discovery of novel fungicidal candidates.

Indole/Tetrahydroquinoline as Renewable Natural Resource-Inspired Scaffolds in the Devising and Preparation of Potential Fungicide Candidates.

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