Direct arylations on water: synthesis of 2,5-disubstituted oxazoles balsoxin and texaline

Ohnmacht, Stephan A.; Mamone, Patrizia; Culshaw, Andrew J.; Greaney, Michael F.

doi:10.1039/b719466h

Cited by 149 publications

(34 citation statements)

References 43 publications

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“…142 Both electron-rich and electron-deficient aryl iodides participated in the reaction, the 5-arylated oxazole products were obtained in high yields. The reaction was utilized in the synthesis of two oxazole-containing natural products, balsoxin and texaline.…”

Section: On Water Reactionsmentioning

confidence: 99%

Organic Synthesis “On Water”

2009

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Section: On Water Reactionsmentioning

confidence: 99%

Organic Synthesis “On Water”

2009

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“…In 2007, Greaney et al. described several examples of Pd‐catalyzed direct arylations of heteroaromatics “on water” . They observed, using this solvent, very clean direct C5‐arylations of thiazoles with high conversions of aryl iodides after 24 h at 60 °C (Scheme , a) .…”

Section: Reactions In Green Solventsmentioning

confidence: 99%

Environmentally Benign Arylations of 5‐Membered Ring Heteroarenes by Pd‐Catalyzed C−H Bonds Activations

Mao

Shi

et al. 2018

ChemCatChem

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The palladium‐catalyzed functionalization of 5‐membered ring heteroaromatics, through a C−H bonds activation, for access to arylated heteroaromatics represent a very attractive alternative to more classical cross‐coupling reactions, as it saves steps and reduces the amount of wastes. Despite these advantages, these transformations initially suffered from major limitations in terms of sustainable chemistry concerning the reaction media, the nature of the catalyst, the catalyst loading, the aryl source or the regioselectivity control. Tremendous improvements allowing more sustainable reaction conditions using greener solvents, new aryl sources or employing easily removable catalysts and lower catalyst loadings have been described during the last decades. This review summarizes some of the most important contributions made in these directions.

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“…Greaney conducted a C5-arylation of oxazole under palladium catalysis on water to access texaline. Their original method was also applied to the synthesis of balsoxin, which displays antimycobacterial activity (Scheme 16.26b) [51]. Hoarau achieved two sequential C-H arylations of oxazole 132 at its C2 and C5 positions, followed by decarboxylation to give texaline [52].…”

Section: Texaline Febuxostat and Muscoride A (C-h Arylation Of Oxazmentioning

confidence: 99%

Synthesis of Natural Products and Pharmaceuticals via Catalytic CH Functionalization

Yamaguchi¹,

Amaike²,

Itami³

2016

Transition Metal‐Catalyzed Heterocycle Synthesis via CH Activation

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Direct arylations on water: synthesis of 2,5-disubstituted oxazoles balsoxin and texaline

Abstract: An efficient two-step palladium catalysed synthesis of 2,5-disubstituted oxazoles is reported.

Cited by 149 publications

References 43 publications

Organic Synthesis “On Water”

Organic Synthesis “On Water”

Environmentally Benign Arylations of 5‐Membered Ring Heteroarenes by Pd‐Catalyzed C−H Bonds Activations

Synthesis of Natural Products and Pharmaceuticals via Catalytic CH Functionalization

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