Tetrahedron letters

Palladium-catalyzed amination of aryl dibromides with secondary amines: synthetic and mechanistic aspects

IP Beletskaya, AG Bessmertnykh, R Guilard

Index: Beletskaya, Irina P.; Bessmertnykh, Alla G.; Guilard, Roger Tetrahedron Letters, 1999 , vol. 40, # 35 p. 6393 - 6397

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Citation Number: 39

Abstract

Diaminobenzenes are obtained starting from m-and p-dibromobenzenes and secondary amines in the presence of Pd (dba) 2/P (o-tolyl) 3and sodium tert-butoxide in moderate to good yields. Reductive dehalogenation of aryl dibromides is a major side reaction under these conditions. The study of this reaction has shown that the formation of reductive dehalogenation products occurs according to two independent ways. The first one ...

 Related Synthetic Route
Piperidine Structure

110-89-4

Piperidine

1,4-Dibromobenzene Structure

106-37-6

1,4-Dibromobenzene

~90%

1-Phenylpiperidine Structure

4096-20-2

1-Phenylpiperidine

Piperidine Structure

110-89-4

Piperidine

1,3-Dibromobenzene Structure

108-36-1

1,3-Dibromobenzene

~0%

1-Phenylpiperidine Structure

4096-20-2

1-Phenylpiperidine

1-(3-piperidin-1-ylphenyl)piperidine Structure

27594-19-0

1-(3-piperidin-...

Piperidine Structure

110-89-4

Piperidine

1,4-Dibromobenzene Structure

106-37-6

1,4-Dibromobenzene

~45%

1-Phenylpiperidine Structure

4096-20-2

1-Phenylpiperidine

1-(4-BROMOPHENYL)PIPERIDINE Structure

22148-20-5

1-(4-BROMOPHENY...

Detail
Piperidine Structure

110-89-4

Piperidine

1,2-Dibromobenzene Structure

583-53-9

1,2-Dibromobenzene

~%

1-Phenylpiperidine Structure

4096-20-2

1-Phenylpiperidine

Piperidine Structure

110-89-4

Piperidine

1,4-Dibromobenzene Structure

106-37-6

1,4-Dibromobenzene

~37%

1-Phenylpiperidine Structure

4096-20-2

1-Phenylpiperidine

1,4-di-(1-piperidinyl)benzene Structure

25556-16-5

1,4-di-(1-piper...

1,4-Dibromobenzene Structure

106-37-6

1,4-Dibromobenzene

Diethylamine Structure

109-89-7

Diethylamine

~44%

1-N,1-N,4-N,4-N-tetraethylbenzene-1,4-diamine Structure

18996-77-5

1-N,1-N,4-N,4-N...

N,N-Diethylaniline Structure

91-66-7

N,N-Diethylaniline

morpholine Structure

110-91-8

morpholine

1,4-Dibromobenzene Structure

106-37-6

1,4-Dibromobenzene

~78%

4-Phenylmorpholine Structure

92-53-5

4-Phenylmorpholine

1,4-Dimorpholinobenzene Structure

4096-22-4

1,4-Dimorpholin...

1,3-Dibromobenzene Structure

108-36-1

1,3-Dibromobenzene

Diethylamine Structure

109-89-7

Diethylamine

~59%

1-N,1-N,3-N,3-N-tetraethylbenzene-1,3-diamine Structure

64287-26-9

1-N,1-N,3-N,3-N...

N,N-Diethylaniline Structure

91-66-7

N,N-Diethylaniline

Piperidine Structure

110-89-4

Piperidine

1,3-Dibromobenzene Structure

108-36-1

1,3-Dibromobenzene

~65%

1-Phenylpiperidine Structure

4096-20-2

1-Phenylpiperidine

1-(3-piperidin-1-ylphenyl)piperidine Structure

27594-19-0

1-(3-piperidin-...

morpholine Structure

110-91-8

morpholine

1,4-Dibromobenzene Structure

106-37-6

1,4-Dibromobenzene

~0%

4-Phenylmorpholine Structure

92-53-5

4-Phenylmorpholine

1,4-Dimorpholinobenzene Structure

4096-22-4

1,4-Dimorpholin...

morpholine Structure

110-91-8

morpholine

1,3-Dibromobenzene Structure

108-36-1

1,3-Dibromobenzene

~0%

1,3-dimorpholinobenzene Structure

51100-94-8

1,3-dimorpholin...

4-Phenylmorpholine Structure

92-53-5

4-Phenylmorpholine

1,3-Dibromobenzene Structure

108-36-1

1,3-Dibromobenzene

Diethylamine Structure

109-89-7

Diethylamine

~0%

1-N,1-N,3-N,3-N-tetraethylbenzene-1,3-diamine Structure

64287-26-9

1-N,1-N,3-N,3-N...

N,N-Diethylaniline Structure

91-66-7

N,N-Diethylaniline

1,4-Dibromobenzene Structure

106-37-6

1,4-Dibromobenzene

Diethylamine Structure

109-89-7

Diethylamine

~0%

1-N,1-N,4-N,4-N-tetraethylbenzene-1,4-diamine Structure

18996-77-5

1-N,1-N,4-N,4-N...

N,N-Diethylaniline Structure

91-66-7

N,N-Diethylaniline


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