Mechanochemical Iridium(III)‐Catalyzed C−H Bond Amidation of Benzamides with Sulfonyl Azides under Solvent‐Free Conditions in a Ball Mill

Hermann, Gary N.; Becker, P.; Bolm, Carsten

doi:10.1002/ange.201511689

Cited by 59 publications

(10 citation statements)

References 78 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Mechanochemistry is a versatile platform for organocatalytic and metal-catalyzed transformations, 59 − 62 such as the Suzuki–Miyaura coupling 63 − 65 Huisgen cycloaddition, 66 olefin metathesis, 67 C–H activation, and more. 68 − 79 Most examples of catalytic mechanochemistry rely on catalysts developed for solution chemistry. However, mechanochemistry offers a very different reaction environment, which can sustain other catalytic designs, and perhaps make previously challenging reactions simpler and more accessible.…”

Section: Catalysis In Mechanochemical Reactionsmentioning

confidence: 99%

Mechanochemistry: A Force of Synthesis

2016

View full text Add to dashboard Cite

The past decade has seen a reawakening of solid-state approaches to chemical synthesis, driven by the search for new, cleaner synthetic methodologies. Mechanochemistry, i.e., chemical transformations initiated or sustained by mechanical force, has been advancing particularly rapidly, from a laboratory curiosity to a widely applicable technique that not only enables a cleaner route to chemical transformations but offers completely new opportunities in making and screening for molecules and materials. This Outlook provides a brief overview of the recent achievements and opportunities created by mechanochemistry, including access to materials, molecular targets, and synthetic strategies that are hard or even impossible to access by conventional means.

show abstract

Section: Catalysis In Mechanochemical Reactionsmentioning

confidence: 99%

Mechanochemistry: A Force of Synthesis

2016

View full text Add to dashboard Cite

show abstract

“…Mechanochemistry Exploiting mechanical energy to run chemical reactions is a relatively recent approach in chemistry that has proved effective in generating the desired products without requiring high temperatures and toxic solvents [24]. Furthermore, the use of mechanochemistry often results in reduced reaction times, increased yields, and uncommon reactivity pathways that are not achievable thermally [29,30]. Lately, mechanochemistry has been extended from classical organic synthesis to the preparation of functional materials, with notable examples including metal-organic frameworks, metal nanoparticles, bioconjugates, carbon allotropes, and perovskites, often resulting in high surface area, porosity, catalytic activity, and stability [24,31].…”

Section: Novel Synthetic Methodologiesmentioning

confidence: 99%

New trends in nonconventional carbon dot synthesis

Bartolomei

Dosso

Prato

2021

Trends in Chemistry

View full text Add to dashboard Cite

Carbon dots (CDs) are currently one of the hot topics in the nanomaterial world. Until recently, their preparation has been mostly based on solvothermal or hydrothermal syntheses requiring high temperatures, long reaction times, or toxic solvents. Moreover, the resulting materials are often affected by low reproducibility and difficult purification. A potential solution to these problems could be represented by innovative fields of chemistry, such as mechanochemistry, flow chemistry, and laser synthesis in the liquid phase. Machine learning could also be applied to go beyond the trial-and-error approach commonly used to explore the CD chemical space. In this review, we explore these recent approaches and their future potential to address some of the CD limitations, widening the range of properties and applications of these highly promising nanomaterials. Synthesis of carbon dots: current challengesCarbon dots (CDs) are currently one of the most studied carbon-based materials, due to their highly promising properties. CDs are carbon-based nanoparticles presenting dimensions <10 nm, emissions ranging over the whole visible spectrum, low toxicity, and long-term photo and colloidal stability [1,2]. Generally, CDs are synthesized following either a top-down or bottomup approach, with the latter more commonly used due to its superior versatility and accessibility [3]. In fact, CD synthesis mostly relies on hydrothermal or solvothermal treatment of relatively small molecular precursors (citric acid, amino acids, carbohydrates, anilines) involving either high temperatures/pressures, long reaction times, or toxic organic solvents [4][5][6][7][8][9][10][11]. This approach is highly appreciated for the simple and economic set up and for the wide range of precursors that can be employed. An improvement in solvothermal synthesis has been achieved by using microwaves. This resulted in a great reduction of reaction times and solvent amount, mainly arising from a more controllable thermal transport [4,12]. Despite these advantages, the high temperatures needed (>150°C) result in multiple reaction pathways that are not clearly predictable, leading to extensive formation of by-products, which are often highly emissive (Figure 1) [13][14][15][16][17]. As a result, various papers identified the presence of molecular fluorophores in CD samples, highlighting the urgent need for more stringent purification protocols [18][19][20][21]23,25]. This aspect, together with irregular heat and mass transfer typical of batch synthesis, often contributes to the low reproducibility observed in CD preparation [4,22]. Furthermore, the procedures used to tailor the obtained materials are still based on a trial-and-error strategy. This approach is limited by the absence of predictability, resulting in long and difficult optimizations of the target properties and extensive time consumption. To go beyond these limitations, approaches able to increase the reproducibility of the synthesis and finely tailor the material characteristics are required. A poss...

show abstract

“…As a consequence of these disappointing results in solution, the strategy was changed and we studied the aforementioned iridium catalysis with 1 a and 10 a as substrates under solvent-free conditions in a ball mill reactor. [20,21] Already the first attempt was successful. Milling 1 a and 10 a in the presence of 2.5 mol % of [Cp*IrCl 2 ] 2 and 2 equiv.…”

Section: Communicationsmentioning

confidence: 99%

1,2‐Benzothiazine Derivatives from Sulfonimidamides by Metal‐Catalyzed Annulation Reactions in Solution and under Solvent‐Free Mechanochemical Conditions

et al. 2021

Self Cite

View full text Add to dashboard Cite

Three‐dimensional aza‐analogues of 1,2‐benzothiazine 1,1‐dioxides have been prepared from sulfonimidamides. Two different protocols are presented. The first is a rhodium‐catalyzed annulation reaction with α‐sulfonyloxyketones leading to 4‐unsubstituted benzothiazine derivatives. By selective bromination with NBS the heterocyclic ring can further be functionalized. In the second approach, an iridium catalyst is applied under solvent‐free mechanochemical conditions providing products with 3,4‐disubstituted thiazine rings from diazoketo esters and diazoketo sulfones.

show abstract

Mechanochemical Iridium(III)‐Catalyzed C−H Bond Amidation of Benzamides with Sulfonyl Azides under Solvent‐Free Conditions in a Ball Mill

Cited by 59 publications

References 78 publications

Mechanochemistry: A Force of Synthesis

Mechanochemistry: A Force of Synthesis

New trends in nonconventional carbon dot synthesis

1,2‐Benzothiazine Derivatives from Sulfonimidamides by Metal‐Catalyzed Annulation Reactions in Solution and under Solvent‐Free Mechanochemical Conditions

Contact Info

Product

Resources

About