[GeorgiaMJ]

So, for organic lab I have to synthesise 9-hexyl-3-bromo-6-nitrocarbazole. In one of my steps , actually my first I need to synthesise carbazole from diphenylamine . The problem is that in the lab Pd(OAc)2 is not available. I searched all the web for an other way to make this step but still I cant find something that doesnt involve Pd(OAC)2. I'm not still so sure about the mechanism of the reaction. So can I use something else instead?

[OrganicDan96]

any other Pd complexes available?

[GeorgiaMJ]

No

[MollyCooL]

It’s highly unlikely but if you have the catalyst, the following paper might help.

Dehydrocyclization of Diphenylamine to Carbazole over Platinum-Based Bimetallic Catalysts
Chinese Journal of Catalysis, 2010, 31 (11–12), 2010, pp 1439-1444
DOI: 10.1016/S1872-2067(10)60129-5

[EngPet]

Here are the reported conditions from the whole web, I hope it helps you

[kriggy]

@MollyCooL: I dont think this conditions are usefull.. Having the catalyst is one thing and  also heating to 400-500°C as they describe is something not commonly done in chemical labs

GeorgiaMJ: why dont you buy the catalyst? Its not as expensive (Fluorochem has 1g for £ 60,00

[zarhym]

You may try this photo irradiation approach.
This is a reaction I have done for many times.


For my reaction, 1g of diphenylsulfide requires about 20mg I₂, 500mL DCM and a quartz flask.
The reaction is completed after 40W UVC bulbs irradiation for 3 hours.

Methyloxirane is an oxidizer to regenerate of I₂, but I find out that it is not very important if I let the reaction done under air.

 

[zarhym]

FYI

The procedure in the attachment is from the supporting info of this paper: [10.1039/c5pp00466g].
By the way, I am the first author and the experiment was done when I was a graduate student.