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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: MatusSK on July 30, 2020, 03:42:46 PM

Title: Pd(PPh3)Cl2 in Stille coupling
Post by: MatusSK on July 30, 2020, 03:42:46 PM

Hello everyone,
I´ve performed a Stille coupling reaction with Pd(PPh3)Cl2 in dry DMF. For coupling reaction it is necessary to use Pd(0) instead of Pd(II). In my case I used only Pd(PPh3)Cl2 without any reducing agent (amines, phosphine) according to literature and reaction worked very well. Does anybody know how I got Pd(0) from Pd(II) in Pd(PPh3)Cl2?
Thank you

Title: Re: Pd(PPh3)Cl2 in Stille coupling
Post by: rolnor on July 30, 2020, 04:36:07 PM

I think it is reduced by the RSn-reagent.

Title: Re: Pd(PPh3)Cl2 in Stille coupling
Post by: MatusSK on July 31, 2020, 02:33:38 AM

How?

Title: Re: Pd(PPh3)Cl2 in Stille coupling
Post by: rolnor on July 31, 2020, 04:01:44 AM

I am not sure but tin can be converted to tin chloride. It can mean that alkyl-tin bond cleaves.

Title: Re: Pd(PPh3)Cl2 in Stille coupling
Post by: kriggy on July 31, 2020, 05:36:19 AM

Could you have PdII - PdIV cycle as well?

Title: Re: Pd(PPh3)Cl2 in Stille coupling
Post by: MatusSK on August 01, 2020, 04:44:49 AM

I dont know. Is it possible?

Title: Re: Pd(PPh3)Cl2 in Stille coupling
Post by: rolnor on August 01, 2020, 08:59:07 AM

Its the tin-reagent or PPh3 that reduces the Pd if I understand correct; https://en.wikipedia.org/wiki/Stille_reaction