Re: ORGLIST: Heck addition of aryl halides to olefins

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From: Faiz Ahmed Khan (faiz$##$iitk.ac.in)
Date: Sat Jun 03 2000 - 07:42:13 EDT

Dear Jack,
By varying the 'catalyst cocktail' you can get either 3-arylpropanal or beta-aryl
allyl alcohol (normal Heck product). For example, additives such as silver(I) or
thallium (I) salts give the latter product predominantly. The following review will
be helpful:
A. de Meijere, F.E. Meyer, Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411.
(see page: 2382)
good luck,
F.A. Khan

Jack Sullivan wrote:

> Pd-catalyzed addition of ArX (X= Br, I) is known to result in mixtures of
> regioisomers when olefins are used that contain electrron-donating substituents.
> My project involves the reaction of these halides with allyl alcohol to give
> 3-arylpropanals. Is anyone familiar with any recent references on varying the
> reaction conditions (halide, catalyst, etc) to minimize or eliminate this side
> product formation? Thank you in advance!
> --
> Jack Sullivan
>
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>
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> List coordinator: Joao Aires de Sousa (jas$##$mail.fct.unl.pt)


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