I bridged thymol and 4-aminophthalonitrile with azo coupling reaction in order to synthesize a ligand for phthalocyanines. I synthesized the ligand with %95 yield but hydroxyl group of thymol did not permit to phthalocyanine formation. So I want to exchange that hydroxyl group with thiol by Newman-Kwart Rearrangement.
I dont know the reaction but palladiumtetrakistriphenylphosphine is a Pd(0) source. So if you are going to use Pd(OAc)2 you need a reducing agent along with it to make Pd(0). Reducing agents are typically phosphines, amines, or water.
My guess would be yes, but then you are just making the same catalyst as the one you are trying to replace. However, you are making it in situ if you use Pd(OAc)2 in combination with PPh3.
Try other phosphines if you want to get creative.
Why are you trying to replace Pd(PPh3)4?
I have no palladiumtetrakistriphenylphosphine, I have different phosphines, but I did not know that it could made like this. It was very helpful thank you very much.
When you are planning to perform a catalytic reaction, you should know your reagent, substrate and their chemical nature, reactivity and properties (N-phile, E-phile) etc. Further, you should know the role of metal complex. You should also know about the oxidation state, coordination number and the number of electron at the metal center. Most of the catalytic reactions are 2e process involving oxidative addition and reductive elimination.
Metals should have two stable oxidation states with a difference of 2e., for example, Pd(0) to Pd(II), Pd(II) to Pd(IV), Rh(I) to Rh(III) like that. Then which one will add in what way, whether it is 3 bond concerted addition or nucleophilic oxidative addition that depends on your reagent. So many things are there; better read some basic concepts and understand chemistry before you touch a catalyst or make your own catalyst.
Chemistry is interesting, fascinating and exciting if we know what we are doing. Greg has already given some hint in this regard. Just mixing two things is not chemistry.
Good Luck
Balakrishna
I suggest if you dont need -OH group, you can add some alkyl halide such as ethyl,propyl, butyl or pentyl/hexyl bromide/chloride. These alkyl halides react with phenol groups and you can obtain -OR, then you can try to synthesize phthalocyanine(s).
Additionally, the azo linkage are not stable during the heating for pc synthesis sometimes.
Another thing that, you can convert the -OH group to -SH group, also this is another problem group, generally -SH groups can bind for -S-S-, and oxidize sometimes, that can be problem for you.
İ think the best way is close the -OH group using alkyl halides.
Good luck
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