Methods of making indole analogs using a rhodium-containing catalyst are described, along with methods of using the compounds to treat hyperglycemic, hyperlipidemic, or autoimmune disorders in mammals, and corresponding pharmaceutical compositions. Disclosed herein is a method of making indoles. The method comprises contacting a reactant of formula I wherein E is a protecting group, —SO2-Aryl, or —SO2-substituted-Aryl; and R and R2 are independently selected from the group consisting of hydrogen, halo, C1-C12-alkyl and aryl; with a rhodium(l)-containing catalyst.

The present invention relates to a simple process for regenerating a hydroformylation catalyst consisting of a heterogenized catalyst system on a support consisting of a porous ceramic material. The invention also relates to a process for the start-up of the hydroformylation reaction after regeneration according to the invention.

Described herein is a hydroformylation catalyst system and method useful for producing aldehydes from olefin substrates, without using carbon monoxide gas. The hydroformylation catalyst system includes a hydroformylation catalyst complex including a Group 9 metal complexed with a phosphine-based ligand; a syngas surrogate including formic acid and an anhydride compound, which forms carbon monoxide in situ; and hydrogen, which may derive from the syngas surrogate or not derived from the syngas surrogate. The method involves reacting the olefin substrate with a syngas surrogate in the presence of a hydroformylation catalyst complex, wherein the syngas surrogate forms carbon monoxide, and optionally hydrogen, in situ, and then isolating the aldehyde compound from a reaction mixture.

This invention relates to a catalyst used in a carbonylation of methanol using carbon monoxide to acetic acid, and more particularly to a heterogeneous catalyst represented by Rh/WxC (where x is an integer of 1 or 2) in which a complex of a rhodium compound and 3-benzoylpyridine is fixed on a support of tungsten carbide.

Embodiments of the present invention relate to processes to prepare a spent catalyst fluid from a hydroformylation process for precious metal recovery. In one embodiment, a process comprises (a) removing a spent catalyst fluid from an active hydroformylation reaction system, wherein the spent catalyst fluid comprises the hydroformylation reaction catalyst and is substantially free of non-hydrolyzable triorganophosphorous compounds; and (b) adding a non-hydrolyzable triorganophosphorous compound to the spent catalyst fluid from step (a) prior to storing the fluid or prior to shipping for precious metal recovery.

Disclosed herein are methods to rejuvenate a deactivated hydroformylation catalyst solution wherein the solution comprises rhodium, polyphosphoramidite ligands, and polyphosphoramidite ligand degradation products. In some embodiments, such methods comprise adding a peroxide to the deactivated hydroformylation catalyst solution.

Certain aspects of the present invention are directed to improved processes for preparing enantiomerically enriched intermediates for the synthesis of ruxolitinib and deuterated forms of ruxolitinib. Certain aspects are also directed to deuterated intermediates useful in the synthesis of deuterated forms of ruxolitinib. Certain aspects are also directed to reaction mixtures for preparing enantiomerically enriched intermediates useful in the synthesis of ruxolitinib and deuterated forms of ruxolitinib.

The present invention generally relates to processes for the recovery of rhodium from a catalyst purge stream from a C6 or higher olefin hydroformylation process. In one embodiment, the process comprises (a) treating a catalyst-containing liquid purge stream from the hydroformylation process, wherein the catalyst comprises a precious metal and an organophosphorous ligand, with an oxidant in the presence of a separate liquid aqueous phase comprising a halide-free acid at a sufficient temperature to effect oxidation of a majority of the contained organophosphorous ligand, wherein the halide-free acid is a C1-C6 organic acid or phosphorous acid; (b) recovering the aqueous phase; (c) contacting the aqueous phase with a separate organic phase by mixing the two phases under a syngas atmosphere, wherein the separate organic phase comprises water-insoluble, hydrolysable organophosphorous ligand and recycled olefin from a hydroformylation process; and (d) separating the organic phase to be recycled back to a hydroformylation process.

Disclosed herein are methods of treating a hydroformylation catalyst solution wherein the solution comprises rhodium, polyphosphoramidite ligands, and polyphosphoramidite ligand degradation products and wherein the hydroformylation catalyst solution is used to hydroformylate an olefin in an operating hydroformylation unit. In some embodiments, such methods comprise contacting the catalyst solution with a peroxide in the operating hydroformylation unit.

Disclosed herein are methods to rejuvenate a deactivated hydroformylation catalyst solution wherein the solution comprises rhodium, polyphosphoramidite ligands, and polyphosphoramidite ligand degradation products. In some embodiments, such methods comprise adding a peroxide to the deactivated hydroformylation catalyst solution.