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.

A Sequential Pd/Norbornene-Catalyzed Process Generateso-Biaryl Carbaldehydes or Ketones via a Redox Reaction or 6H-Dibenzopyrans by C–O Ring Closure / Motti, Elena; DELLA CA', Nicola; D., Xu; A., Piersimoni; Bedogni, Elena; Z. M., Zhou; Catellani, Marta. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 14:12(2012), pp. 5792-5795. [10.1021/ol302889t]

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

MOTTI, Elena;DELLA CA', Nicola;BEDOGNI, Elena;CATELLANI, Marta
2012-01-01

Abstract

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.
2012
A Sequential Pd/Norbornene-Catalyzed Process Generateso-Biaryl Carbaldehydes or Ketones via a Redox Reaction or 6H-Dibenzopyrans by C–O Ring Closure / Motti, Elena; DELLA CA', Nicola; D., Xu; A., Piersimoni; Bedogni, Elena; Z. M., Zhou; Catellani, Marta. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 14:12(2012), pp. 5792-5795. [10.1021/ol302889t]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2528086
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