Commonwealth Scientific and Industrial Research Organisation

Boron Molecular Pty Limited

Boron Molecular Limited

Helmut Weigold

Sebastian Mario Marcuccio

Mary Rodopoulos

Peter Osvath

The invention relates to processes for the synthesis of aryl or alkene borates which comprises reacting: (i) an olefinic compound having a halogen or halogen-like substituent in a vinylic substitution position, or (ii) an aromatic ring having a halogen or halogen-like substituent in a ring substitution position, with a disubstituted monohydroborane in the presence of a Group 8&#x2013;11 metal catalyst. The invention also relates to the use of these borates in coupling reactions. The invention further relates to certain disubstituted monohydroboranes and aryl or alkene borates.

Hydroboronation process

The invention relates to a process for the preparation of organic boronic acid derivatives involving the reaction of an organic compound with diboronic acid in the presence of a Group 8-11 metal catalyst.

Process for preparing organic boronic acid derivatives using diboronic acid

The invention provides a process for covalently coupling organic compounds which comprises reacting an aromatic ring compound having a halogen or halogen-like substituent at a coupling position with a diboron derivative in the presence of a Group VIII metal catalyst and a suitable base. The invention also provides useful arylboron intermediates.

Aryl borates

The invention relates to a process for the preparation of an organic boronic acid derivative comprising reacting a penta- or hexa-substituted diboron derivative with an organic compound having a halogen or halogen-like substituent at a coupling position in the presence of a Group VIII metal catalyst, such that a direct carbon to boron bond is formed between said coupling position and a boron-containing residue of the penta- or hexa-substituted diboron derivative.

Substituted diboron compounds

This invention relates to a process for covalently coupling organic compounds which comprises: reacting an olefinic compound having at least one carbon to carbon double bond or an acetylenic compound having at least one carbon to carbon triple bond with a diboron derivative in the presence of a Group 8-11 metal catalyst to form an organoboron intermediate having an organoboronate residue on at least one carbon atom of the respective double or triple bond; and reacting the organoboron intermediate with an organic compound having a halogen or halogen-like substituent at a coupling position in the presence of a Group 8-11 metal catalyst and a suitable base, whereby the olefinic or acetylenic compound is coupled to the organic compound via a direct bond between the carbon atom having the organoboronate residue and the coupling posiitijno. This invention also relates to a process for preparing an organoboron derivative which comprises reacting an olefinic compound having a leaving group in at the allylic position with a diboron derivative in the presence of a Group 8-11 metal catalyst such that the leaving gruop is replaced with an organoboronate residue. The invention further relates to organoborn intermediates and their preparation.

Organoboron derivatives and process for coupling organic compounds

The invention relates to processes for the synthesis of aryl or alkene borates which comprises reacting: (i) an olefinic compound having a halogen or halogen-like substituent in a vinylic substitution position, or (ii) an aromatic ring having a halogen or halogen-like substituent in a ring substitution position, with a disubstituted monohydroborane in the presence of a Group 8-11 metal catalyst. The invention also relates to the use of these borates in coupling reactions. The invention further relates to certain disubstituted monohydroboranes and aryl or alkene borates.

A process for the preparation of a diboronic acid ester comprising contacting diboronic acid with a suitable monoalcohol, diol or polyol, for a time and under conditions such that the diboronic acid reacts with the monoalcohol, diol or polyol to form the diboronic acid ester.

Boronic compounds

This invention describes a process for covalently coupling organic compounds which comprises reacting an olefinic compound having a halogen or halogen-like substituent at a coupling position with a diboron derivative in the presence of a Group VIII metal catalyst and a suitable base. The invention also describes a process for preparing alkene borate intermediates comprising reacting an olefinic compound having a halogen or halogen-like substituent with a diboron derivative in the presence of a Group VIII metal catalyst and a suitable base.

Alkene borates and a process for covalently coupling organic compounds

The invention provides a process for covalently coupling organic compounds which comprises reacting an aromatic ring compound having a halogen substituent or other substituent which undergoes substitution with a diboronic acid ester at a coupling position with a diboron derivative in the presence of a Group VIII metal catalyst and a suitable base.

This invention relates to a diboron derivative of formula (I) or a diboron derivative of formula (II) or a diboron derivative of formula (III) where R , R , R and R are each independently selected from the group consisting of optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, a group of the formula &mdash;(R Q) R where Q is selected from O, S, NR , optionally substituted arylene and optionally substituted cycloalkylene, m is an integer selected from 1 to 3, the or and each R is independently an optionally substituted C -C alkylene, R is C -C alkyl or hydrogen, and R is hydrogen or C -C alkyl; each X is independently selected from O, S(O) and NR , where n is an integer from 0 to 3, R is hydrogen or C -C alkyl, or one or more of &mdash;NR R , &mdash;NR R , &mdash;NR R and &mdash;NR R represent an optionally substituted 5 or 6 membered heterocyclyl group,and A, A and A are divalent groups which may or may not be different.

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Mount Waverley, Australia

Helmut Weigold