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Boronic acids and derivatives from borylation of aryl and vinyl derivatives via Pd coupling with diisopropylamino borane

Référence

85054-01

Statut des brevets

French patent FR-01 16734 filed on December 21, 2001 entitled “(Aryl)(Amino) Borane compounds, Method for preparing same”

Inventeurs

Michel VAULTIER
Gilles ALCAREZ
Christophe DURIEZ
Lisenn EUZENAT
Yann RIBOURDOUILLE

 

Statut commercial

Commercial Status Non-exclusive licence, R&D Partnership

Laboratoire

Laboratoire de Chimie et Photonique Moléculaires http://www.UMR6510.univ-rennes1.fr/

Description

CONTEXT

Arylboronic acids and esters are generally prepared by borylation of aromatic organomagnesium or organolithium derivatives. These methods are expensive, require specific conditions and are not general, which renders them rather unattractive. The aim of the invention is to provide boranes, which can be used in particular in a
coupling reaction, that is to say a reaction for the borylation of various derivatives, which can be prepared by a simple process, which exhibit sufficient stability to be stored and which can be readily refunctionalized.

TECHNICAL DESCRIPTION

The invention concerns (aryl)(amino)borane compounds and a method for preparing these compounds. These molecules are of formula A-BH-N R1R2.

Wherein R1 andR2 are selected among linear branched or he compound are obtained by a method which consists in preparing an amineborane R1R2NHBH3 complex, in transforming it into aminoborane R1R2NBH2 by heating, then in reacting it with an A-X compound where X is a leaving group.

The compounds can be used as reactant for various reactions and in particular for Suzuki- Miyaura couplings.

A few specific reactions are illustrated below by way of examples by a reaction scheme given in each of the cases in which R1=R2 and A is a phenyl group carrying a Z substituent=iPr. Of course similar reactions can be carried out using amino borane compounds obtained from amines other than diisopropyalamine.

INDUSTRIAL APPLICATIONS

Custom synthesis.

DEVELOPMENT STAGE

Already positively tested on an industrial scale.

RELATED PUBLICATIONS

Stereospecific palladium-catalyzed borylation reaction of 1-alkenyl halides with diispropylaminoborane. Journal of Organometallic Chemistry  (2005),  690(11),  2721-2724.

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