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A Sequential Pd/Norbornene-Catalyzed Process Generates o-Biaryl Carbaldehydes or Ketones via a Redox Reaction or 6H‑Dibenzopyrans by C–O Ring Closure

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journal contribution
posted on 2012-11-16, 00:00 authored by Elena Motti, Nicola Della Ca’, Di Xu, Anna Piersimoni, Elena Bedogni, Zhi-Ming Zhou, Marta Catellani
o-Biaryl carbaldeydes and ketones are obtained through the one-pot reaction of o-aryl iodides with o-bromobenzyl alcohols under the catalytic action of Pd and norbornene, in the presence of a base. The same reaction can also give dibenzopyrans by Pd and norbornene catalysis with a different termination, leading to C–O ring closure. In both cases the process first leads to a five-membered palladacycle, which controls C–C coupling, then to a seven-membered oxapalladacycle, which gives aldehydes and ketones or dibenzopyrans.

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