Journal of the American Chemical Society

Mechanisms and models for copper mediated nucleophilic aromatic substitution. 2. Single catalytic species from three different oxidation states of copper in an …

AJ Paine

Index: Paine, Anthony James Journal of the American Chemical Society, 1987 , vol. 109, # 5 p. 1496 - 1502

Full Text: HTML

Citation Number: 234

Abstract

Abstract: Ullmann condensation of diarylamines with iodobenzenes has been investigated under homogeneous and heterogeneous catalytic conditions with cuprous and curpic salts, as well as powdered copper metal. Copper catalyzed condensation of diarylamines with iodoaromatics is relatively insensitive to substituent (for substituted iodobenzenes p=-0.25; for substituted diphenylamines p= 1.09) but quite sensitive to halogen (kI/kB,> 200). The ...

 Related Synthetic Route
1,4-Diiodobenzene Structure

624-38-4

1,4-Diiodobenzene

N-Phenyl-1-naphthalenamine Structure

90-30-2

N-Phenyl-1-naph...

~60%

N,N,N',N'-Tetraphenyl-1,4-phenylenediamine Structure

14118-16-2

N,N,N',N'-Tetra...

Iodobenzene Structure

591-50-4

Iodobenzene

1,4-Diiodobenzene Structure

624-38-4

1,4-Diiodobenzene

Diphenylamine Structure

122-39-4

Diphenylamine

~%

N,N,N',N'-Tetraphenyl-1,4-phenylenediamine Structure

14118-16-2

N,N,N',N'-Tetra...

Detail
Iodobenzene Structure

591-50-4

Iodobenzene

4-Iodo-N,N-diphenylaniline Structure

38257-52-2

4-Iodo-N,N-diph...

Diphenylamine Structure

122-39-4

Diphenylamine

~%

N,N,N',N'-Tetraphenyl-1,4-phenylenediamine Structure

14118-16-2

N,N,N',N'-Tetra...

Detail
Iodobenzene Structure

591-50-4

Iodobenzene

3-Chlorodiphenylamine Structure

101-17-7

3-Chlorodipheny...

~86%

3-chloro-N,N-diphenylaniline Structure

106336-13-4

3-chloro-N,N-di...

1-Chloro-3-iodobenzene Structure

625-99-0

1-Chloro-3-iodo...

3-Chlorodiphenylamine Structure

101-17-7

3-Chlorodipheny...

~84%

3-chloro-N,N-diphenylaniline Structure

106336-13-4

3-chloro-N,N-di...

Iodobenzene Structure

591-50-4

Iodobenzene

1-Chloro-3-iodobenzene Structure

625-99-0

1-Chloro-3-iodo...

Diphenylamine Structure

122-39-4

Diphenylamine

~%

Triphenylamine Structure

603-34-9

Triphenylamine

Detail
Benzenamine,N-phenyl-3-(trifluoromethyl)- Structure

101-23-5

Benzenamine,N-p...

1-Iodonaphthalene Structure

90-14-2

1-Iodonaphthalene

~57%

NAPHTHALEN-1-YL-DIPHENYL-AMINE Structure

61231-45-6

NAPHTHALEN-1-YL...

Iodobenzene Structure

591-50-4

Iodobenzene

N-Phenyl-1-naphthalenamine Structure

90-30-2

N-Phenyl-1-naph...

~88%

Triphenylamine Structure

603-34-9

Triphenylamine

Benzenamine,N-phenyl-3-(trifluoromethyl)- Structure

101-23-5

Benzenamine,N-p...

Iodobenzene Structure

591-50-4

Iodobenzene

~75%

N,N-diphenyl-3-(trifluoromethyl)aniline Structure

106336-12-3

N,N-diphenyl-3-...

m-iodobenzotrifluoride Structure

401-81-0

m-iodobenzotrif...

N-Phenyl-1-naphthalenamine Structure

90-30-2

N-Phenyl-1-naph...

~63%

N,N-diphenyl-3-(trifluoromethyl)aniline Structure

106336-12-3

N,N-diphenyl-3-...

Iodobenzene Structure

591-50-4

Iodobenzene

m-iodobenzotrifluoride Structure

401-81-0

m-iodobenzotrif...

Diphenylamine Structure

122-39-4

Diphenylamine

~%

Triphenylamine Structure

603-34-9

Triphenylamine

Detail
1,4-Diiodobenzene Structure

624-38-4

1,4-Diiodobenzene

N-Phenyl-1-naphthalenamine Structure

90-30-2

N-Phenyl-1-naph...

~42%

4-Iodo-N,N-diphenylaniline Structure

38257-52-2

4-Iodo-N,N-diph...

3-Iodotoluene Structure

625-95-6

3-Iodotoluene

3-Chlorodiphenylamine Structure

101-17-7

3-Chlorodipheny...

~84%

3-methyl-N,N-diphenylaniline Structure

4316-54-5

3-methyl-N,N-di...

Iodobenzene Structure

591-50-4

Iodobenzene

3-Iodotoluene Structure

625-95-6

3-Iodotoluene

Diphenylamine Structure

122-39-4

Diphenylamine

~%

Triphenylamine Structure

603-34-9

Triphenylamine

Detail

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