Synthesis

A domino copper-catalyzed CN and CO cross-coupling for the conversion of primary amides into oxazoles

K Schuh, F Glorius

Index: Schuh, Kerstin; Glorius, Frank Synthesis, 2007 , # 15 p. 2297 - 2306

Full Text: HTML

Citation Number: 37

Abstract

Abstract A variety of oxazoles can efficiently be prepared, in a single step and in good yield, from primary amides and 1, 2-dihaloalkenes using copper-catalysis. This new method allows the regioselective formation of a range of substituted oxazoles. The required 1, 2- dihaloalkenes can prepared by simple treatment of alkynes with elemental bromine or iodine.

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N-(2-iodo-2-phenylvinyl)acetamide Structure

952429-63-9

N-(2-iodo-2-phe...

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2-METHYL-5-PHENYLOXAZOLE Structure

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Acetamide Structure

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2-METHYL-5-PHENYLOXAZOLE Structure

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Acetamide Structure

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~21%

2-METHYL-5-PHENYLOXAZOLE Structure

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2-METHYL-5-PHEN...

2-methyl-4-phenyloxazole Structure

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Phenylacetylene Structure

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Phenylacetylene

~%

2-METHYL-5-PHENYLOXAZOLE Structure

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N/A Structure

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N/A

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2-METHYL-5-PHENYLOXAZOLE Structure

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5-(trimethylsilyl)-2,4-diphenyloxazole Structure

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Oxazole, 2,4-diphenyl Structure

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((7-OXO-7H-BENZ(DE)ANTHRACEN-3-YL)THIO)-ACETICACI Structure

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N/A Structure

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N/A

Benzamide Structure

55-21-0

Benzamide

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2,5-Diphenyloxazole Structure

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2,5-Diphenyloxazole

Oxazole, 2,4-diphenyl Structure

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Oxazole, 2,4-di...

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Benzamide Structure

55-21-0

Benzamide

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Oxazole, 2,4-diphenyl Structure

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Phenylacetylene Structure

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trimethylsilylethynylbenzene Structure

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Oxazole, 2,4-diphenyl Structure

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(Z)-1,2-dibromo-1-(trimethylsilyl)-2-phenylethylene Structure

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Oxazole, 2,4-diphenyl Structure

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Oxazole, 2,4-di...

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Acetamide Structure

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2-METHYL-5-PHENYLOXAZOLE Structure

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Acetamide Structure

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2-METHYL-5-PHENYLOXAZOLE Structure

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2-METHYL-5-PHEN...

2-methyl-4-phenyloxazole Structure

20662-90-2

2-methyl-4-phen...

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Phenylacetylene Structure

536-74-3

Phenylacetylene

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2-methyl-4-phenyloxazole Structure

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2-methyl-4-phen...

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((7-OXO-7H-BENZ(DE)ANTHRACEN-3-YL)THIO)-ACETICACI Structure

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2-(4-methoxyphenyl)-4-phenyl-1,3-oxazole Structure

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2-(4-methoxyphenyl)-5-phenyl-1,3-oxazole Structure

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