Unsymmetric Chiral Ligands for Large Metallo‐Macrocycles: Selectivity of Orientational Self‐Sorting DOI Creative Commons
Ondřej Jurček,

Subhasis Chattopadhyay,

Elina Kalenius

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(36)

Published: June 7, 2024

Abstract Nature uses various chiral and unsymmetric building blocks to form substantial complex supramolecular assemblies. In contrast, the majority of organic ligands used in metallosupramolecular chemistry are symmetric achiral. Here we extend group bile acids as a scaffold for bispyridyl by employing chenodeoxycholic acid (CDCA), an epimer previously ursodeoxycholic (UDCA). The epimerism, flexibility, bulkiness leads large structural differences coordination products upon reaction with Pd(NO 3 ) 2 . UDCA‐bispyridyl ligand self‐assembles quantitatively into single crown‐like Pd L 6 complex, whereas CDCA provides mixture complexes general formula n 2n , i.e., 4 8 5 10 even 12 containing impressive 120 centers. were studied combination analytical methods, ion‐mobility mass spectrometry (IM‐MS) providing valuable details on their structure allowed effective separation m/z 1461 individual signals according arrival time distribution, thereby revealing four different ions [Pd (NO ] 3+ 4+ 5+ 6+ structures all modelled using DFT calculations. Finally, challenges conclusions determining specific identity these species discussed.

Language: Английский

2‐Benzamide Tellurenyl Iodides: Synthesis and Their Catalytic Role in CO2 Mitigation DOI
Saket Jain, Monojit Batabyal, Raviraj Ananda Thorat

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(49)

Published: June 20, 2023

Benzamide-derived organochalcogens (chalcogen=S, Se, and Te) have shown promising interest in biological synthetic chemistry. Ebselen molecule derived from benzamide moiety is the most studied organoselenium. However, its heavier congener organotellurium under-explored. Here, an efficient copper-catalyzed atom economical method has been developed to synthesize 2-phenyl-benzamide tellurenyl iodides by inserting a tellurium into carbon-iodine bond of 2-iodobenzamides one pot with 78-95 % yields. Further, Lewis acidic nature Te center basic nitrogen synthesized 2-Iodo-N-(quinolin-8-yl)benzamide enabled them as pre-catalyst for activation epoxide CO2 at 1 atm preparation cyclic carbonates TOF TON values 1447 h-1 4343, respectively, under solvent-free conditions. In addition, 2-iodo-N-(quinolin-8-yl)benzamide also used activating anilines form variety 1,3-diaryl ureas up 95 yield. The mechanistic investigation mitigation done 125 NMR HRMS studies. It seems that reaction proceeds via formation catalytically active Te-N heterocycle, ebtellur intermediate which isolated structurally characterized.

Language: Английский

Citations

11
Unified and green oxidation of amides and aldehydes for the Hofmann and Curtius rearrangements DOI
Liyan Song,

Yufei Meng,

Tongchao Zhao

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 26(1), P. 428 - 438

Published: Nov. 27, 2023

The oxone–halide green oxidation system is extended to the of primary amides and aromatic aldehydes (with sodium azide) generate N -haloamide acyl azides, respectively, for subsequent Hofmann Curtius rearrangements.

Language: Английский

Citations

9
Ring Opening of N-Acyl Lactams Using Nickel-Catalyzed Transamidation DOI

Karthik Rajan Rajamanickam,

Sunwoo Lee

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(2), P. 1336 - 1344

Published: Jan. 4, 2024

We successfully developed a nickel-catalyzed transamidation method for the ring opening of N-acyl lactams. The involves reaction between N-benzoylpyrrolidin-2-one derivatives and aniline derivatives, with Ni(PPh3)2Cl2 serving as catalyst, 2,2′-bipyridine ligand, manganese reducing agent. This led to formation ring-opening-amidated products in good yields. Notably, exhibited excellent efficiency producing corresponding ring-opening various sizes, including four-, five-, six-, seven-, eight-membered

Language: Английский

Citations

3
Efficient and Sustainable Electrosynthesis of N-Sulfonyl Iminophosphoranes by the Dehydrogenative P–N Coupling Reaction DOI Creative Commons

Jessica C. Bieniek,

Darryl Nater,

Sara L. Eberwein

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(6), P. 2188 - 2196

Published: April 18, 2024

Iminophosphoranes are commonly used reagents in organic synthesis and are, therefore, of great interest. An efficient sustainable iodide-mediated electrochemical N-sulfonyl iminophosphoranes from readily available phosphines sulfonamides is reported. This method features low amounts supporting electrolytes, inexpensive electrode materials, a simple galvanostatic setup, high conversion rates. The broad applicability could be demonstrated by synthesizing 20 examples yields up to 90%, having diverse functional groups including chiral moieties biologically relevant species. Furthermore, electrolysis was performed on g scale run repetitive mode recycling the electrolyte, which illustrates suitability for large-scale production. A reaction mechanism involving mediation iodide-based electrolyte proposed, completely agreeing with all results.

Language: Английский

Citations

3
Synthesis of Acyl Hydrazides from Carboxamides and Hydrazine Hydrate Under Metal‐Free Conditions at Room Temperature DOI
Shweta Singh, Jeyakumar Kandasamy

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(6)

Published: March 30, 2023

Abstract Synthesis of acyl hydrazides from amides has been achieved at room temperature through N ‐activation reactions. A wide spectrum functionalized primary and secondary was initially converted into ‐Boc, ‐nitroso ‐tosyl subjected to transamidation with hydrazine hydrate obtain the desired in 76–94% yields. Broad substrate scope, shorter reaction time mild conditions are merits developed methodology.

Language: Английский

Citations

6
Base-Mediated Synthesis of Anhydrides from Activated Amides DOI
Iliyasu Aliyu Bashir, Sunwoo Lee

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 6159 - 6167

Published: April 17, 2023

Symmetrical anhydrides were synthesized from activated amides such as N-benzoylsaccharins and N-Boc-protected benzamides. The reacted with H2O in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) at 25 °C to produce corresponding symmetrical high yields through C-N bond cleavage. In addition, benzoic acid derivatives generate unsymmetrical yields.

Language: Английский

Citations

6
Reductive cross-coupling of N-acyl pyrazole and nitroarene using tetrahydroxydiboron: synthesis of secondary amides DOI

Hayeon Moon,

Sunwoo Lee

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(41), P. 8329 - 8334

Published: Jan. 1, 2023

We report on a new method for the synthesis of amides using acyl pyrazoles and nitroarenes under reducing conditions. It was found that react with organo-nitro compounds in presence B2(OH)4, giving corresponding good yields. demonstrated benzoyl having various substituents different can be used to produce range N-substituted benzamides. The shows functional group tolerance has potential application variety organic molecules.

Language: Английский

Citations

6
Synthesis of Acyl Hydrazides and Hydrazones from Activated Amides DOI
Sunwoo Lee,

Miso Kim

Synthesis, Journal Year: 2024, Volume and Issue: 56(14), P. 2263 - 2269

Published: Feb. 15, 2024

Abstract Acyl hydrazide and acyl hydrazone synthesis methods were developed. They involve the reaction of an activated amide with hydrazine under transition-metal-catalyst-free conditions. Additionally, hydrazones synthesized by extending same procedure in presence aldehydes (or ketones). These reactions performed aqueous environment at 25 °C, demonstrating successful attainment desired compounds high yields.

Language: Английский

Citations

2
Catalyst-free activation of N–C(O) Amide bonds – efficient cascade synthesis of N-acyl thiocarbamides in batch and continuous-flow DOI
Karthick Govindan, Nian‐Qi Chen, Wei‐Yu Lin

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(9), P. 5187 - 5193

Published: Jan. 1, 2024

We developed, a sustainable approach for the direct synthesis of activated amides ( N -acyl saccharin) into divergent thiocarbamide derivatives using thiocyanate salts and 2-MeTHF as green solvent.

Language: Английский

Citations

2
Amide N–C Bond Activation: A Graphical Overview of Acyl and Decarbonylative Coupling DOI Creative Commons
Chengwei Liu, Michal Szostak

SynOpen, Journal Year: 2023, Volume and Issue: 07(01), P. 88 - 101

Published: Feb. 14, 2023

Abstract This Graphical Review provides an overview of amide bond activation achieved by selective oxidative addition the N–C(O) acyl to transition metals and nucleophilic addition, resulting in decarbonylative coupling, together with key mechanistic details pertaining distortion underlying this reactivity manifold.

Language: Английский

Citations

5