Palladium‐Catalyzed Aminocarbonylation Reaction to Access 1,3,4‐Oxadiazoles using Chloroform as the Carbon Monoxide Source

Li, Zhengyi; Wang, Liang

doi:10.1002/adsc.201500778

Cited by 45 publications

(10 citation statements)

References 42 publications

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“…Similar type of reaction mechanism was mentioned in various transformations for the insertion of carbon monoxide. Palladium catalysed aroylation of NH‐sulfoximines (Scheme 57<xschr57), aminocarbonylation of amines (Scheme ), aminocarbonylation of tetrazoles (Scheme ), aminocarbonylation of indoles (Scheme ) and aminocarbonylation of imidazopyridines (Scheme ) has been established using CHCl 3 as carbonyl source.…”

Section: Reaction Solvents As Precursors For the Installation Of Key mentioning

confidence: 99%

Reaction Medium as the Installing Reservoir for Key Functionalities in the Molecules

2019

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The solvent is an important entity in a chemical reaction, generally, required for the effective collision of the reactant molecules. By looking at the chemical nature, physic-chemical properties, and more importantly, smart selection, reaction solvents attract synthetic chemists for their effective use as reagents in a chemical reaction. For the installation of small key functionalities in the molecules, reaction solvents provide attractive, atom-economical, greener, and also less costly alternatives to other reagent-based strategies. For instance, particular reaction solvents can serve as a multipurpose building block for various units, such as O,

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Section: Reaction Solvents As Precursors For the Installation Of Key mentioning

confidence: 99%

Reaction Medium as the Installing Reservoir for Key Functionalities in the Molecules

2019

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“…Alkyl chloride units, especially polychlorinated hydrocarbons, are a very important class of functional groups, which are widely found in bioactive molecules such as pharmaceuticals and pesticides [1] . Simultaneously, polychlorinated hydrocarbons units also can further transformed into a variety of new compounds, including aldehyde, [2a–d] ester, [2e–h] ketone, [2i–n] carboxylic acid, [2o–r] alkene, [2s–t] carbene, [2u–x] etc [2y–z] . Therefore, the formation of polychlorinated alkane units have been well established over the past few decades.…”

Section: Introductionmentioning

confidence: 99%

Recent Developments in the Polychloroalkylation by Use of Simple Alkyl Chlorides

Liang

Ouyang

et al. 2020

Adv Synth Catal

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Owing to their easy availability and cheapness, simple alkyl chlorides are good raw materials for introducing complex polychlorinated groups. Polychlorinated hydrocarbons units, such as di‐ or trichloromethyl groups, not only widely found in pesticide and bioactive molecule, but also can be as a precursor to converted into different functional groups such as −COOH, −CHO and −CO. The direct polychloroalkylation reaction by using simple alkyl chlrides has been considered to be an important tool for synthesizing complex polychlorinated compounds. This review summarizes recent developments, especially free radical strategies, in the polychloroalkylation of different substrates (such as 2‐acylpyridines, benzyl tertiary amines, alkenes, imine and 1,n‐enynes). We hope that this review provides a new perspective on this field and also provides a reference to develop environmentally friendly and sustainable methods.

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“…Recently, the use of chloroform as a CO surrogate has grabbed the attention of organic chemists for the synthesis of a variety of targeted organic molecules . The in situ ‐generated CO from CHCl 3 and a base has been used in various organic reactions such as carboxylation, carbonylative coupling, aminocarbonylations, Heck‐type domino cyclization, and carbonylative Sonogashira coupling . Recently, one of us has elegantly demonstrated the application of this methodology (chloroform as CO surrogates) in aminocarbonylation of 7‐azaindole and imidazopyridines, leading to the synthesis of biologically important aminocarbonyl‐functionalized 7‐azaindole and 2‐amidoimidazo[1,2‐ a ]pyridines .…”

Section: Introductionmentioning

confidence: 99%

Carbonylative Suzuki coupling reactions catalyzed by ONO pincer–type Pd(II) complexes using chloroform as a carbon monoxide surrogate

Layek

Agrahari

Ganguly

et al. 2020

Applied Organom Chemis

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Benzoylhydrazone Schiff base–ligated three new ONO pincer–type palladium(II) complexes, [(PdL1(PPh3)] (1), [(PdL2(PPh3)] (2), and [(PdL3(PPh3)] (3), were synthesized by the reaction of the respective ligand, N‐(2‐hydroxybenzylidene)benzohydrazide (HL1), N‐(2‐hydroxy‐3‐methoxybenzylidene)benzohydrazide (HL2), or N‐(5‐bromo‐2‐hydroxybenzylidene) benzohydrazide (HL3), with Pd(OAc)2 and PPh3 in methanol and isolated as air‐stable reddish‐orange crystalline solids in high yields (78%–83%). All three complexes were fully characterized by elemental analysis, Fourier‐transform infrared spectroscopy, UV–Visible, 1H nuclear magnetic resonance (NMR), 13C{1H} NMR, and 31P{1H} NMR spectroscopic studies. The molecular structure of all three complexes was established unambiguously by single‐crystal X‐ray diffraction studies which revealed a distorted square planar geometry of all three complexes. The ONO pincer–type ligands occupied three coordination sites at the palladium, while the fourth site is occupied by the monodentate triphenylphosphine ligand. The catalytic potential of all three complexes was explored in the carbonylative Suzuki coupling of aryl bromides and iodides with arylboronic acids to yield biaryl ketones, using CHCl3 as the source of carbonyl. The reported protocol is convenient and safe as it obviates the use of carbon monoxide (CO) balloons or pressured CO reactors which are otherwise needed for the carbonylation reactions. The methodology has been successfully applied to the synthesis of two antineoplastic drugs, namely, phenstatin and naphthylphenstatin, in good yields (81% and 85%, respectively). Under the optimized reaction conditions, complex 2 exhibited the best catalytic activity in the carbonylative Suzuki couplings. The reported catalysts have wide reaction scope with good functional group tolerance. All catalysts could be retrieved from the reaction after completion and recycled up to three times with insignificant loss in the catalytic activity.

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Palladium‐Catalyzed Aminocarbonylation Reaction to Access 1,3,4‐Oxadiazoles using Chloroform as the Carbon Monoxide Source

Cited by 45 publications

References 42 publications

Reaction Medium as the Installing Reservoir for Key Functionalities in the Molecules

Reaction Medium as the Installing Reservoir for Key Functionalities in the Molecules

Recent Developments in the Polychloroalkylation by Use of Simple Alkyl Chlorides

Carbonylative Suzuki coupling reactions catalyzed by ONO pincer–type Pd(II) complexes using chloroform as a carbon monoxide surrogate

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