A process to produce 1-octene and 1-decene includes (a) separating a composition containing an oligomer product—which contains 15 to 80 mol % C.sub.6 olefins, 20 to 80 mol % C.sub.8 olefins, and 5 to 20 mol % C.sub.10+ olefins—into a first oligomer composition containing C.sub.6 alkanes and at least 85 mol % C.sub.6 olefins (e.g., 1-hexene), a second oligomer composition containing at least 20 mol % C.sub.8 olefins (e.g., 1-octene), and a heavies stream containing C.sub.10+ olefins, then (b) contacting a metathesis catalyst system with the first oligomer composition to form a first composition comprising C.sub.10 linear internal olefins, (c) contacting the C.sub.10 linear internal olefins with a catalytic isomerization catalyst system in the presence of photochemical irradiation to form a second composition comprising 1-decene, and (d) purifying the second composition to isolate a third composition comprising at least 90 mol % 1-decene. Processes to produce 1-hexene and 1-decene also are described, as well as related manufacturing systems and processes to produce higher carbon number normal alpha olefins from lower carbon number normal alpha olefins.

Catalyst systems suitable for tetramerizing ethylene to form 1-octene may include a catalyst having a structure according to Formula (VI) or Formula (VII). In Formulas (VI) and (VII), X is a halogen, a (C.sub.2-C.sub.30) carboxylate, acetylacetonate, or a (C.sub.1-C.sub.30) hydrocarbyl; L.sub.1 is a neutral coordinating ligand; n is an integer from 0 to 6; Y is a (C.sub.6-C.sub.20)fluorine-substituted aryl, a (C.sub.6-C.sub.20)fluorine-substituted aryloxy, or a (C.sub.1-C.sub.20)fluorine-substituted alkoxy; and L∩L is a bidentate chelating ligand. The catalyst system may also include an aluminum containing agent which includes a reaction product of an organoaluminum compound and an antifouling compound. The antifouling compound may include one or more quaternary salts.

A process for the production of 4-hydroxybutyraldehyde is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of methylcyclohexane as a reaction solvent and a catalyst system comprising a rhodium complex and a substituted or unsubstituted diphosphine ligand. The use of the methylcyclohexane increases the reaction rate while also giving a high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde and improving the separation of the hydroxyaldehyde products from the catalyst system.

Described herein is the preparation of a 1,3,5-triazinyl benzimidazole and chemical intermediates used in the synthetic process.

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.

Gold (I) complexes that can absorb light in the near-UV and/or visible regions and methods of making and using thereof are described. These gold (I) complexes have photochemical reactivities, such as strong absorption of near-UV and/or visible light, quenching rate constants ≥3.5×10.sup.5 s.sup.−1, etc., that allow them to catalyze photoredox reactions, such as homocoupling of organic halides (e.g. alkyl halides and aryl halides), alkylation of 2-phenyl-1,2,3,4-tetrahydroisoquinoline, cyclization of indoles, reductive dehalogenation of aryl halides, and/or C—H bonds cleavage, under near-UV and/or visible light. The product of a photo-induced organic reaction catalyzed by the gold (I) complexes described herein can have a yield that is higher than the yield of the same product formed from the same reaction under the same reaction conditions, using the same loading or a higher loading of [Au.sub.2(μ-dppm).sub.2](Cl).sub.2, [Ru(bpy).sub.3](Cl).sub.2, and/or [fac-Ir(ppy).sub.3] compared to the loading of the one or more gold (I) complex(es).

Disclosed are a chiral multidentate ligand (I), a preparation, and an application thereof. In this method, compound (M1) is subjected to condensation with compound (M2) followed by amine deprotection in the presence of a deprotection reagent to obtain compound (M4). Compound (1) is subjected to deprotonation by butyl lithium and phosphorization followed by dimethylamino group substitution to produce compound (3). The compound (3) and the compound (M4) are reacted in the presence of triethylamine to produce chiral multidentate ligands.

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A process for the production of 4-hydroxybutyraldehyde is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of methylcyclohexane as a reaction solvent and a catalyst system comprising a rhodium complex and a substituted or unsubstituted diphosphine ligand. The use of the methylcyclohexane increases the reaction rate while also giving a high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde and improving the separation of the hydroxyaldehyde products from the catalyst system.

Methods for preparing the Bruton's Tyrosine Kinase (“BTK”) inhibitor compound 2-{3′-hydroxymethyl-1-methyl-5-[5-((S)-2-methyl-4-oxetan-3-yl-piperazin-1-yl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-[3,4′]bipyridinyl-2′-yl}-7,7-dimethyl-3,4,7,8-tetrahydro-2H,6H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one are provided. Methods for preparing tricyclic lactam compounds are also provided.

Catalyst systems suitable for tetramerizing ethylene to form 1-octene may include a catalyst having a structure according to Formula (VI) or Formula (VII). In Formulas (VI) and (VII), X is a halogen, a (C.sub.2-C.sub.30) carboxylate, acetylacetonate, or a (C.sub.1-C.sub.30) hydrocarbyl; L.sub.1 is a neutral coordinating ligand; n is an integer from 0 to 6; Y is a (C.sub.6-C.sub.20)fluorine-substituted aryl, a (C.sub.6-C.sub.20)fluorine-substituted aryloxy, or a (C.sub.1-C.sub.20)fluorine-substituted alkoxy; and L∩L is a bidentate chelating ligand. The catalyst system may also include an aluminum containing agent which includes a reaction product of an organoaluminum compound and an antifouling compound. The antifouling compound may include one or more organic acids, organic acid salts, esters, anhydrides, or combinations of these.