Catalyst ligands, catalyst compositions, catalyst metal complexes and processes for cross-coupling aromatic boron compounds with aromatic halogens or perfluoroalkylsulfonates
AssigneeSymyx Technologies, Inc.
InventorsAnil Guram, Xiaohong Bei, Timothy S. Powers, Bernd Jandeleit, Thomas Crevier
Life of this patent
Estimating the term…
Abstract
The present invention discloses new organic compounds (e.g., ligands), their metal complexes and compositions using those compounds. The invention also relates to the field of catalysis. In particular, this invention relates to new compounds which when combined with suitable metals or metal precursor compounds provide useful catalysts for various bond-forming reactions, including Suzuki cross-coupling reactions. The invention also relates to performing Suzuki cross coupling reactions with unreactive aryl-chlorides.
Claims30
A ligand characterized by one of the general formulas:
- ##STR40## wherein each R.sup.1 and R.sup.2 is independently selected from the group consisting of alkyl, substituted alkyl, cycloalkyl and substituted cycloalkyl;
- each R.sup.3, R.sup.4 and R.sup.5 is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, aryloxy, silyl, boryl, phosphino, amino, thio, seleno, and combinations thereof;
- and optionally, R.sup.3 and R.sup.4 are joined together in a ring structure;
- each R.sup.6 and R.sup.7 is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, aryloxy, silyl, boryl, phosphino, amino, thio, seleno, water solubilizing groups, transition metals and combinations thereof;
- b is 0, 1, 2, 3 or 4;
- c is 0, 1, 2 or 3;
- and optionally two or more R.sup.6 or R.sup.7 groups are joined together in a ring structure.
A ligand characterized by one of the general formulas:
- ##STR41## wherein each R.sup.1 and R.sup.2 is independently selected from the group consisting of alkyl, substituted alkyl, cycloalkyl and substituted cycloalkyl;
- R.sup.5 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, aryloxy, silyl, boryl, phosphino, amino, thio, seleno, and combinations thereof;
- and optionally, R.sup.3 and R.sup.4 are joined together in a ring structure;
- each R.sup.6 and R.sup.7 is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, aryloxy, silyl, boryl, phosphino, amino, thio, seleno, water solubilizing groups, transition metals and combinations thereof;
- b is 0, 1, 2, 3 or 4;
- c is 0, 1, 2 or 3;
- and optionally two or more R.sup.6 or R.sup.7 groups are joined together in a ring structure.
A process for preparing polycyclic aromatic compounds by cross-coupling of a first aromatic compound with a second aromatic compounds in the presence of a base, a solvent, a metal precursor and a ligand that is characterized by any of the following formulas:
- ##STR42## wherein each R.sup.1 and R.sup.2 is independently selected from the group consisting of alkyl, substituted alkyl, cycloalkyl and substituted cycloalkyl;
- each R.sup.3, R.sup.4 and R.sup.5 is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, aryloxy, silyl, boryl, phosphino, amino, thio, seleno, and combinations thereof;
- and optionally, R.sup.3 and R.sup.4 are joined together in a ring structure;
- each R.sup.6 and R.sup.7 is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, heteroalkyl, heterocycloalkyl, substituted heterocycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkoxy, aryloxy, silyl, boryl, phosphino, amino, thio, seleno, water solubilizing groups, transition metals and combinations thereof;
- b is 0, 1, 2, 3 or 4;
- c is 0, 1, 2 or 3;
- and optionally two or more R.sup.6 or R.sup.7 groups are joined together in a ring structure.
Dependencies are inferred from the claim text.