e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synlett

Copper (II) Acetate Catalyzed Cross-Coupling of Pentafluorophenylboronic Acid with Amines under an Atmosphere of Oxygen

W Zhong, Z Liu, C Yu, W Su

Index: Zhong, Weihui; Liu, Zhenyu; Yu, Chuanming; Su, Weike Synlett, 2008 , # 18 p. 2888 - 2892

Full Text: HTML

Citation Number: 9

Abstract

Abstract Under an atmosphere of oxygen and a catalytic amount of Cu (OAc) 2, pentafluorophenylboronic acid reacted with anilines at room temperature to produce the corresponding N-pentafluorophenylanilines in moderate to good yields. In the case of alkylamines, unexpected N-alkyl-2, 2′, 3, 3′, 4′, 5, 5′, 6, 6′-nona-fluoro-biphenyl-4- amines were formed under the similar conditions in moderate yields.

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

Structure

~70%

Pentafluorobenzene Structure

Pentafluorobenzene

Decafluorobiphenyl Structure

Decafluorobiphenyl

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

p-Toluidine Structure

~0%

Pentafluorobenzene Structure

Pentafluorobenzene

Decafluorobiphenyl Structure

Decafluorobiphenyl

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

p-Anisidine Structure

~0%

2,3,4,5,6-pentafluoro-N-(4-methoxyphenyl)aniline Structure

2,3,4,5,6-penta...

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2-Amino-p-xylene Structure

2-Amino-p-xylene

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

~0%

N/A Structure

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

3,5-Difluoroaniline Structure

3,5-Difluoroaniline

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

~0%

N-(3,5-difluorophenyl)-2,3,4,5,6-pentafluoroaniline Structure

N-(3,5-difluoro...

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

4-Chloroaniline Structure

4-Chloroaniline

~0%

N-(4-chlorophenyl)-2,3,4,5,6-pentafluoroaniline Structure

N-(4-chlorophen...

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

Structure

~0%

Pentafluorobenzene Structure

Pentafluorobenzene

Decafluorobiphenyl Structure

Decafluorobiphenyl

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

3-Toluidine Structure

~0%

N/A Structure

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

3,4-Difluoroaniline Structure

3,4-Difluoroaniline

~0%

N/A Structure

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

2,3,4-Trifluoroaniline Structure

2,3,4-Trifluoro...

~0%

N/A Structure

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

3-Chloroaniline Structure

3-Chloroaniline

~0%

N/A Structure

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2-Ethylaniline Structure

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

~0%

N/A Structure

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

3-Chloro-2-methylaniline Structure

3-Chloro-2-meth...

~0%

N/A Structure

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2,6-Diisopropylaniline Structure

2,6-Diisopropyl...

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

~0%

N/A Structure

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

p-Toluidine Structure

~0%

Pentafluorobenzene Structure

Pentafluorobenzene

Decafluorobiphenyl Structure

Decafluorobiphenyl

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

p-Anisidine Structure

~0%

2,3,4,5,6-pentafluoro-N-(4-methoxyphenyl)aniline Structure

2,3,4,5,6-penta...

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2-Amino-p-xylene Structure

2-Amino-p-xylene

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

~0%

N/A Structure

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

3,5-Difluoroaniline Structure

3,5-Difluoroaniline

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

~0%

N-(3,5-difluorophenyl)-2,3,4,5,6-pentafluoroaniline Structure

N-(3,5-difluoro...

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

4-Chloroaniline Structure

4-Chloroaniline

~0%

N-(4-chlorophenyl)-2,3,4,5,6-pentafluoroaniline Structure

N-(4-chlorophen...

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

Structure

~0%

Pentafluorobenzene Structure

Pentafluorobenzene

Decafluorobiphenyl Structure

Decafluorobiphenyl

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

3-Toluidine Structure

~0%

N/A Structure

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

3,4-Difluoroaniline Structure

3,4-Difluoroaniline

~0%

N/A Structure

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

2,3,4-Trifluoroaniline Structure

2,3,4-Trifluoro...

~0%

N/A Structure

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

3-Chloroaniline Structure

3-Chloroaniline

~0%

N/A Structure

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2-Ethylaniline Structure

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

~0%

N/A Structure

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

3-Chloro-2-methylaniline Structure

3-Chloro-2-meth...

~0%

N/A Structure

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

2,6-Diisopropylaniline Structure

2,6-Diisopropyl...

2,3,4,5,6-Pentafluorobenzeneboronic acid Structure

2,3,4,5,6-Penta...

~0%

N/A Structure

Pentafluorobenzene Structure

Pentafluorobenzene

Detail

Chemistry and kinetics of singlet pentafluorophenylnitrene

[Poe, Russell; Schnapp, Karlyn; Young, Mary J.T.; Grayzar, Jennifer; Platz, Matthew S. Journal of the American Chemical Society, 1992 , vol. 114, # 13 p. 5054 - 5067]

Chemistry and kinetics of singlet pentafluorophenylnitrene

[Poe, Russell; Schnapp, Karlyn; Young, Mary J.T.; Grayzar, Jennifer; Platz, Matthew S. Journal of the American Chemical Society, 1992 , vol. 114, # 13 p. 5054 - 5067]

Chemistry and kinetics of singlet pentafluorophenylnitrene

[Poe, Russell; Schnapp, Karlyn; Young, Mary J.T.; Grayzar, Jennifer; Platz, Matthew S. Journal of the American Chemical Society, 1992 , vol. 114, # 13 p. 5054 - 5067]

Chemistry and kinetics of singlet pentafluorophenylnitrene

[Poe, Russell; Schnapp, Karlyn; Young, Mary J.T.; Grayzar, Jennifer; Platz, Matthew S. Journal of the American Chemical Society, 1992 , vol. 114, # 13 p. 5054 - 5067]

Disubstitution on hexafluorobenzene with formanilides

[Koppang, R. Journal of Fluorine Chemistry, 1995 , vol. 74, # 2 p. 177 - 180]