A Cooperative Rhodium/Secondary Phosphine Oxide [Rh/P(O)nBu2] Template for Catalytic Hydrodefluorination of Perfluoroarenes DOI Creative Commons
Wei‐Chieh Chang, Helena Randel, Thomas Weyhermüller

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(23)

Published: March 1, 2023

The selective activation of C-F bonds under mild reaction conditions remains an ongoing challenge bond activation. Here, we present a cooperative [Rh/P(O)nBu2 ] template for catalytic hydrodefluorination (HDF) perfluoroarenes. In addition to substrates presenting electron-withdrawing functional groups, the system showed exceedingly rare tolerance electron-donating functionalities and heterocycles. high chemoselectivity catalyst its readiness be deployed at preparative scale illustrate practicality. Empirical mechanistic studies density theory (DFT) study have identified rhodium(I) dihydride complex as catalytically relevant species determining role phosphine oxide fragment. Altogether, demonstrate that molecular templates based on these design elements can assembled create catalysts with increased reactivity challenging activations.

Language: Английский

Copper-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Nitrobenzaldehydes with Aldehydes: Application toward the Synthesis of Natural Products DOI
Subrata Sahoo, Shantanu Pal

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(24), P. 18067 - 18080

Published: Nov. 23, 2021

A novel, efficient, and atom-economical approach for the construction of quinazolinones from 2-nitrobenzaldehydes has been unveiled via copper-catalyzed nitrile formation, hydrolysis, reduction in one pot first time. In this reaction, urea is used as a source nitrogen hydrazine hydrate both nitro group hydrolysis nitrile, atmospheric oxygen sole oxidant. The method portrays wide substrate scope with good functional tolerances. Moreover, was applied synthesis schizocommunin, tryptanthrin, phaitanthrin-A, phaitanthrin-B, 8H-quinazolino[4,3-b]quinazolin-8-one.

Language: Английский

Citations

23
Controlling Chemoselectivity of Catalytic Hydroboration with Light DOI Creative Commons
Enrico Bergamaschi,

Danijela Lunic,

Liam A. McLean

et al.

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 61(8)

Published: Dec. 14, 2021

The ability to selectively react one functional group in the presence of another underpins efficient reaction sequences. Despite many designer catalytic systems being reported for hydroboration reactions, which allow introduction a handle cross-coupling or act as mild method reducing polar functionality, these platforms rarely deal with more complex where multiple potentially reactive sites exist. Here we demonstrate, first time, use light distinguish between ketones and carboxylic acids molecules. By taking advantage different activation modes, single system can be used hydroboration, chemoselectivity dictated only by absence visible light.

Language: Английский

Citations

23
Palladium-Catalyzed Decarbonylative Cyanation of Carboxylic Acids with TMSCN DOI

Tianhao Xu,

Wenhui Li, Kang Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(17), P. 11871 - 11879

Published: Aug. 11, 2022

The direct decarbonylative cyanation of benzoic acids with TMSCN was achieved through palladium catalysis. By this strategy, a wide range nitriles including those functional groups synthesized in good to high yields. Moreover, reaction applied modifying bioactive molecules such as adapalene, probenecid, telmisartan, and 3-methylflavone-8-carboxylic acid. These results demonstrate that new has potential synthetic value organic synthesis.

Language: Английский

Citations

15
Ammonia surrogates in the synthesis of primary amines DOI

Julia Urbiña-Alvarez,

Sergio Rincón-Carvajal,

Diego Gamba‐Sánchez

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(35), P. 7036 - 7051

Published: Jan. 1, 2023

This review provides a comprehensive summary of the utilization ammonia replacements in synthesizing protected and free primary amines, encompassing both traditional reagents latest developments.

Language: Английский

Citations

9
A bio-based click reaction leading to the dihydropyridazinone platform for nitrogen-containing scaffolds DOI
Jiayue Chen, Yao‐Bing Huang, Bin Hu

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(7), P. 2672 - 2680

Published: Jan. 1, 2023

The first biomass-based click reaction is reported to synthesize DHMP from biomass and through transformation.

Language: Английский

Citations

7
Synthesis, Characterization, and Catalytic Study of Caffeine-Derived N-heterocyclic Carbene Palladium Complexes DOI

Qiaoqiao Teng,

Yaru Zhao, Yuchen Lu

et al.

Organometallics, Journal Year: 2022, Volume and Issue: 41(2), P. 161 - 168

Published: Jan. 12, 2022

Homo- and heterodicarbene palladium complexes bearing caffeine-derived N-heterocyclic carbene ligands were synthesized fully characterized by NMR spectroscopy, mass spectrometry, X-ray diffraction analysis. The superior acidity of the alkylated caffeine-based salts also allowed isolation zwitterionic caffeine monocarbene complexes, which showed outperforming catalytic activities in cyanation reactions aryl halides.

Language: Английский

Citations

11
Programing a cyanide-free transformation of aldehydes to nitriles and one-pot synthesis of amides through tandem chemo-enzymatic cascades DOI Creative Commons

Haoteng Zheng,

Qinjie Xiao,

Feiying Mao

et al.

RSC Advances, Journal Year: 2022, Volume and Issue: 12(28), P. 17873 - 17881

Published: Jan. 1, 2022

A chemo-enzymatic cascade was developed for the cyanide-free synthesis of nitriles from aldehydes and further one-pot transformation into amides.

Language: Английский

Citations

10
Kinetic Analysis of Consecutive/Parallel Transformation of Furfural to Biomass-Based Primary Amide by Using a “Concentration–Time” Integral DOI
Shengwen Yang, Jinzhu Chen

ACS Catalysis, Journal Year: 2022, Volume and Issue: 13(1), P. 113 - 131

Published: Dec. 12, 2022

A fundamental understanding of biomass-based transformation furfural (1a) to 2-furamide (4a) is highly desirable for the extension amide chemistry. In this research, direct amidation 1a with hydroxylamine 4a was investigated by using a Cu-doped Co3O4 (Cu/Co3O4) catalyst 2-furancarboxaldehyde oxime (2a) and 2-furonitrile (3a) as detectable intermediates. Mechanism research has demonstrated presence two competitive, independent, parallel reaction pathways: (i) 2a-to-4a rearrangement (the Williams mechanism), (ii) 2a-to-3a dehydration followed 3a-to-4a rehydration classic mechanism) rate-determining step. Subsequent kinetic analysis "concentration–time" integrals revealed that mechanism always predominant pathway, rate constant being almost 22 times greater than mechanism. The catalytic performance Cu/Co3O4 correlated its surface concentration oxygen vacancy acidity. insights thus highlight complex consecutive/parallel aldehyde product.

Language: Английский

Citations

10
Catalytic dehydrative amide bond formation using aqueous ammonia: synthesis of primary amides utilizing diboronic acid anhydride catalysis DOI
Naoya Takahashi,

H. IWASAWA,

Tatsuhito Kinashi

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(48), P. 7391 - 7394

Published: Jan. 1, 2023

Although aqueous ammonia is an inexpensive and readily available safe source of ammonia, there have been no successful studies on direct catalytic dehydrative amidations carboxylic acids with ammonia. In this study, we report a methodology for the synthesis primary amides through diboronic acid anhydride (DBAA)-catalyzed condensation as amine substrate.

Language: Английский

Citations

6
A Cooperative Cobalt-Driven System for One-Carbon Extension in the Synthesis of (Z)-Silyl Enol Ethers from Aldehydes: Unlocking Regio- and Stereoselectivity DOI Creative Commons
Soumyashree Jena,

Lars Frenzen,

Vishal Chugh

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(51), P. 27922 - 27932

Published: Dec. 12, 2023

The research presented herein explores a cobalt-based catalytic system, distinctively featuring cooperative boron-centric element within its intricate ligand architecture. This system is strategically engineered to enable the integration of singular carbon atom into aldehydes, process culminating in production (Z)-silyl enol ethers. Beyond offering an efficient one-pot synthesis route, this method adeptly overcomes challenges inherent conventional techniques, such as need for large amounts additives, restrictive functional group tolerance, and extreme reaction temperatures. Initial mechanistic studies suggest potential role cobalt–carbene complex catalytically significant species underscore importance borane segment. Collectively, these observations highlight advancing bond activation pursuits.

Language: Английский

Citations

4