Alkene borates and a process for covalently coupling organic compounds
AssigneeCommonwealth Scientific and Industrial Research Organisation
InventorsSebastian Mario Marcuccio, Mary Rodopoulos, Helmut Weigold
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Abstract
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.
Claims57
A process for covalently coupling organic compounds which comprises reacting an olefinic compound having a halogen or halogen-like substituent at a vinylic coupling position with a diboron derivative in the presence of a Group VIII metal catalyst and a suitable base.
6 A process according to claim 5 wherein the organic compound is different from the olefinic compound.
A process according to any one of clams 5 to 8 wherein the organic compound is an aliphatic compound having a halogen or halogen-like substituent.
A process according to any one of clams 5 to 8 wherein the organic compound is an allylic compound having a halogen or halogen-like substituent.
A process according to any one of clams 5 to 8 wherein the organic compound is an acetylenic compound having a halogen or halogen-like substituent.
A process for preparing alkene borate intermediates comprising reacting an olefinic compound having a halogen or halogen-like substituent and an active hydrogen containing substituent with a diboron derivative in the presence of a Group VIII metal catalyst and a suitable base.
A process for preparing alkene borate intermediates comprising reacting an olefinic compound having a halogen or halogen-like substituent with a diboron derivative in a protic solvent, DMSO, DMF, dioxane, DME, diethyl ether, THF or a mixture thereof in the presence of a Group VIII metal catalyst and a suitable base.
Novel alkene borates selected from the group consisting of
- 2-(1,2-dimethylprop-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane,
- 2-(1,2-dimethylprop-1-enyl)-5,5-dimethyl-1,3,2-dioxaborinane,
- 5,5-dimethyl-2-(1,2,2-triphenylvinyl)-1,3,2-dioxaborinane,
- 4,4,5,5-tetramethyl-2-(1,2,2-triphenylvinyl)-1,3,2-dioxaborolane,
- ethyl (Z)-2(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl ether,
- 4,4-dimethyl-2-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclo-hex-2-en-1-one,
- (E)-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-enenitrile,
- ethyl (Z)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-enoate,
- 2-bicyclo[3.2.1]oct-2-en-3yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and 1,2,2-triphenylvinylboronic acid.
A process for covalently coupling organic compounds which comprises:
- reacting an olefinic compound having a halogen or halogen-like substituent at a vinylic coupling position with diboron derivative in the presence of a Group VIII metal catalyst and a suitable base to form an alkene borate intermediate;
- adding a mild oxidising agent to decompose excess diboron derivative;
- and
- reacting the alkene intermediate with an organic compound having a halogen or halogen-like substituent at a coupling position in the presence of a Group VIII metal catalyst and a suitable base whereby the olefinic compound is coupled to the organic compound via a direct bond between respective coupling positions.
Dependencies are inferred from the claim text.