Pd(0)–PhCOOH catalyzed addition of oxygen pronucleophiles to allenes and internal alkynes

We have developed a catalytic system that enables the addition of alcohols to allenes using a combination of 5 mol% Pd(PPh3)4 and 10 mol% benzoic acid. Likewise, the addition reaction of carboxylic acids to alkynes is described. In all cases the reaction proceeded well, giving the corresponding allylation products in good-to-high yields with high regio- and stereoselectivities.Key words: addition, alcohols, carboxylic acids, allenes, alkynes, palladium.

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Gold(i)-catalyzed addition of carboxylic acids to internal alkynes in aqueous medium

Organic & Biomolecular Chemistry ◽

10.1039/c6ob02800d ◽

2017 ◽

Vol 15 (7) ◽

pp. 1670-1679 ◽

Cited By ~ 14

Author(s):

Pedro J. González-Liste ◽

Sergio E. García-Garrido ◽

Victorio Cadierno

Keyword(s):

Aqueous Medium ◽

Carboxylic Acids ◽

Catalytic System ◽

Mild Conditions ◽

Broad Scope ◽

Internal Alkynes

A broad scope catalytic system for the intermolecular addition of carboxylic acids to internal alkynes, in water under mild conditions, has been developed.

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Recyclable and reusable PdCl2(PPh3)2/PEG-400/H2O system for the hydrophenylation of alkynes with sodium tetraphenylborate

Journal of Chemical Research ◽

10.1177/1747519820934379 ◽

2020 ◽

pp. 174751982093437

Author(s):

Rong Liu ◽

Tingli Zhang ◽

Bin Huang ◽

Mingzhong Cai

Keyword(s):

Catalytic Activity ◽

Petroleum Ether ◽

Catalytic System ◽

Room Temperature ◽

Sodium Tetraphenylborate ◽

Peg 400 ◽

Apparent Loss ◽

Internal Alkynes ◽

High Yields

A stable and efficient PdCl2(PPh3)2/PEG-400/H2O catalytic system for the hydrophenylation reaction of alkynes has been developed. In the presence of 3 mol% PdCl2(PPh3)2 and 2 equiv. of HOAc, the hydrophenylation of both terminal and internal alkynes with sodium tetraphenylborate proceeded smoothly in a mixture of PEG-400 and water at room temperature or 50 °C to afford a variety of phenyl-substituted alkenes in moderate to high yields. The isolation of the products was easily performed by extraction with petroleum ether, and the PdCl2(PPh3)2/PEG-400/H2O system could be readily recycled and reused six times without apparent loss of catalytic activity.

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Coupling of carboxylic acids with internal alkynes by supported ruthenium catalysts: direct and selective syntheses of multi-substituted phthalide derivatives

Chemical Communications ◽

10.1039/c4cc08461f ◽

2015 ◽

Vol 51 (9) ◽

pp. 1654-1657 ◽

Cited By ~ 23

Author(s):

Hiroki Miura ◽

Kentaro Tsutsui ◽

Kenji Wada ◽

Tetsuya Shishido

Keyword(s):

Carboxylic Acids ◽

Ruthenium Catalysts ◽

Aromatic Carboxylic Acids ◽

Ru Catalyst ◽

Internal Alkynes ◽

High Yields

Supported ruthenium catalysts promote coupling of various kinds of aromatic carboxylic acids with internal alkynes, giving the corresponding multi-substituted phthalide derivatives in high yields. The supported Ru catalyst can be recycled at least five times with no loss of activity.

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Synthesis of 3-(Cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8- carboxylic Acids Via an Efficient Three-component Condensation Reaction between Cyclohexylisocyanide and 2-Aminopyridine-3-carboxylic Acid in the Presence of Aromatic Aldehyde

Combinatorial Chemistry & High Throughput Screening ◽

10.2174/1386207321666180416153112 ◽

2018 ◽

Vol 21 (4) ◽

pp. 298-301 ◽

Cited By ~ 3

Author(s):

Ghasem Marandi

Keyword(s):

Biological Sciences ◽

Carboxylic Acid ◽

Carboxylic Acids ◽

High Performance ◽

Condensation Reaction ◽

Aromatic Aldehydes ◽

New Materials ◽

One Pot ◽

High Yields ◽

Benzaldehyde Derivatives

Aim and Objective: The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. Material and Methods: The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. Results: In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. Conclusion: In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.

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Synthesis and Antiproliferative Evaluation of 2-Deoxy-N-glycosylbenzotriazoles/imidazoles

Molecules ◽

10.3390/molecules26123742 ◽

2021 ◽

Vol 26 (12) ◽

pp. 3742

Author(s):

Caleigh S. Garton ◽

Noelle K. DeRose ◽

Dylan Dominguez ◽

Maria L. Turbi-Henderson ◽

Ashley L. Lehr ◽

...

Keyword(s):

Cell Lines ◽

Cancer Cell ◽

Addition Reaction ◽

Protecting Group ◽

Human Breast ◽

Lung Cancer Cell ◽

Subsequent Removal ◽

Anticancer Properties ◽

Tributyltin Hydride ◽

High Yields

A series of 2-deoxy-2-iodo-α-d-mannopyranosylbenzotriazoles was synthesized using the benzyl, 4,6-benzylidene and acetyl protected D-glucal in the presence of N-iodosuccinimide (NIS). Subsequent removal of the iodine at the C-2 position using tributyltin hydride under free radical conditions afforded the 2-deoxy-α-d-glucopyranosylbenzotriazoles in moderate to high yields. This method was extended to the preparation of substituted 2-deoxy-β-d-glucopyranosylimidazoles as well. The stereoselectivity of the addition reaction and the effect of the protecting group and temperature on anomer distribution of the benzotriazole series were also investigated. The anticancer properties of the newly synthesized compounds were evaluated in a series of viability studies using HeLa (human cervical adenocarcinoma), human breast and lung cancer cell lines. The N-[3,4,6-tri-O-benzyl-2-deoxy-α-d-glucopyranosyl]-1H-benzotriazole and the N-[3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl]-2H-benzotriazole were found to be the most potent cancer cell inhibitors at 20 µM concentrations across all four cell lines.

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Copper-catalyzed 1,6-conjugate addition of para-quinone methides with diborylmethane

Organic Chemistry Frontiers ◽

10.1039/d1qo00632k ◽

2021 ◽

Author(s):

Xin Li ◽

Guoliang Gao ◽

Songtao He ◽

Qiuling Song

Keyword(s):

Catalytic System ◽

Conjugate Addition ◽

Quinone Methides ◽

High Yields

Presented herein is the first 1,6-conjugate addition of diborylmethane, which is promoted by a simple and inexpensive copper catalytic system. This method features high yields, good selectivities and broad functional...

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