26305-75-9

Usage

Uses

Used in Organic Synthesis:
Chlorotris(triphenylphosphine)cobalt(I) is used as a stoichiometric reducing agent for the radical dimerization of halogenated organic molecules. This application is particularly useful in the synthesis of complex organic compounds, as it allows for the selective formation of desired products with high yields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Chlorotris(triphenylphosphine)cobalt(I) is employed as a reducing agent in the synthesis of various drug molecules. Its ability to selectively reduce specific functional groups makes it a valuable tool in the development of new pharmaceutical compounds.
Used in Material Science:
Chlorotris(triphenylphosphine)cobalt(I) is also used in material science for the synthesis of novel materials with unique properties. Its reducing capabilities enable the formation of new compounds that can be used in various applications, such as in the development of advanced electronic devices or in the creation of new materials with improved mechanical properties.
Overall, Chlorotris(triphenylphosphine)cobalt(I) is a versatile and valuable reducing agent that finds applications in various industries, including organic synthesis, pharmaceuticals, and material science. Its ability to selectively reduce specific functional groups and promote the formation of desired products makes it an essential tool in the development of new compounds and materials.

Reaction

Cobalt(I)-catalyzed, steroselective olefination of alkylzinc reagents with aryl aldehydes. Reagent for the reductive radical dimerization of 3-haloindoline derivatives. Cobalt-catalyzed, asymmetric addition of silylacetylene to 1,1-disubstituted allenes.

Upstream product

• 14126-40-0 CoCl₂(PPh₃)3 
• 14126-40-0 bis(triphenylphosphine)dichlorocobalt(II) 
• 15133-82-1 tetrakis(triphenylphosphine)nickel⁽⁰⁾ 
• 7646-79-9 cobalt(II) chloride 
• 14264-16-5 bis(triphenylphosphine)nickel(II) chloride 
• 603-35-0 triphenylphosphine 
• 7646-85-7 zinc(II) chloride 
• 71179-59-4 CoH₂(Si(CH₃)F₂)(P(C₆H₅)3)3 
• 34482-46-7 CoH₂(SiF₃)(P(C₆H₅)3)3 
• 34482-45-6 CoH₂(Si(OC₂H₅)3)(P(C₆H₅)3)3 

Downstream Products

• 883456-17-5 [Co(η4-cis-1,2,3,4-tetraphenylbuta-1,3-diene)(η5-C5H4C(O)CH3)] 
• 12427-78-0 (η4-tetraphenylcyclobutadiene)(η5-cyclopentadienylcarboxaldehyde)cobalt 
• 97073-73-9 (triphenylphosphine)3cobalt(I) tirmethylsilanolate 
• 80243-31-8 Co((C₆H₅)2PCHCHP(C₆H₅)2)2⁽¹⁺⁾*BF₄^(1-) 
• 104041-60-3 (η5-methoxycarbonylcyclopentadienyl)(η4-1,5-cyclooctatetraene)cobalt 
• 75895-97-5 (phthaloyl)bis(triphenylphosphino)(chloro)cobalt 

Relevant academic research and scientific papers

Hydrodimerization of Methyl Acrylate Catalyzed by Halogenotris(triphenylphosphine)cobalt

Methyl acrylate was hydrodimerized in a methanolic solution by CoX(PPh3)3 (X = halogen) into dimethyl adipate.The in situ prepared cobalt complexes from cobalt halides, triphenylphosphine, and zinc gave higher yields of the hydrodimer in the presence of alkali halides.A mechanism is proposed which involves the protonation of Co(I)-methyl acrylate ?-complex to give (2-methoxycarbonylethyl)cobalt complex, followed by a further addition of methyl acrylate.

Cobalt-Catalyzed 1,4-Aryl Migration/Desulfonylation Cascade: Synthesis of α-Aryl Amides

A cobalt-catalyzed 1,4-aryl migration/disulfonylation cascade applied to α-bromo N-sulfonyl amides was developed. The reaction was highly chemoselective, allowing the preparation of α-aryl amides possessing a variety of functional groups. The method was used as the key step to synthesize an alkaloid, (±)-deoxyeseroline. Mechanistic investigations suggest a radical process.

Olefin Hydroarylation Catalyzed by a Single-Component Cobalt(-I) Complex

A single-component Co(-I) catalyst, [(PPh3)3Co(N2)]Li(THF)3, has been developed for olefin hydroarylations with (N-aryl)aryl imine substrates. More than 40 examples were examined under mild reaction conditions to afford the desired alkyl-arene product in good to excellent yields. Catalysis occurs in a regioselective manner to afford exclusively branched products with styrene-derived substrates or linear products for aliphatic olefins. Electron-withdrawing functional groups (e.g., -F, -CF3, and -CO2Me) were tolerated under the reaction conditions.

Mechanistic Interrogation of Alkyne Hydroarylations Catalyzed by Highly Reduced, Single-Component Cobalt Complexes

Highly reactive catalysts for ortho-hydroarylations of alkynes have previously been reported to result from activation of CoBr2 by Grignard reagents, but the operative mechanism and identity of the active cobalt species have been undefined. A mechanistic analysis of a related system, involving hydroarylations of a (N-aryl)aryl ethanimine with diphenylacetylene, was performed using isolable reduced Co complexes. Studies of the stoichiometric reaction of Co(I) or Co(II) precursors with CyMgCl implicated catalyst initiation via a β-H elimination/deprotonation pathway. The resulting single-component Co(-I) complex is proposed as the direct pre-catalyst. Michaelis-Menten enzyme kinetic studies provide mechanistic details regarding the catalytic dependence on substrate. The (N-aryl)aryl ethanimine substrate exhibited saturation-like behavior, whereas alkyne demonstrated a complex dependency; rate inhibition and promotion depend on the relative concentration of alkyne to imine. Activation of the aryl C-H bond occurred only in the presence of coordinated alkyne, which suggests operation of a concerted metalation-deprotonation (CMD) mechanism. Small primary isotope effects are consistent with a rate-determining C-H cleavage. Off-cycle olefin isomerization catalyzed by the same Co(-I) active species appears to be responsible for the observed Z-selectivity.

Simpler and Cleaner Synthesis of Variously Capped Cobalt Nanocrystals Applied in the Semihydrogenation of Alkynes

Unlike the classical organometallic approach, we report here a synthetic pathway requiring no reducing sources or heating to produce homogeneous hexagonal-close-packed cobalt nanocrystals (Co NCs). Involving a disproportionation process, this simple and fast (6 min) synthesis is performed at room temperature in the presence of ecofriendly fatty alcohols to passivate Co NCs. Through a recycling step, the yield of Co NCs is improved and the waste generation is limited, making this synthetic route cleaner. After an easy exchange of the capping ligands, we applied them as unsupported catalysts in the stereoselective semihydrogenation of alkynes.

Alkene isomerization-hydroboration promoted by phosphine-ligated cobalt catalysts

Generated in situ from air-stable cobalt precursors or readily synthesized using NaHBEt3, (PPh3)3CoH(N2) was found to be an effective catalyst for the hydroboration of alkenes. Unlike previous base-metal catalysts for alkene isomerization-hydroboration which favor the incorporation of boron at terminal positions, (PPh3)3CoH(N2) promotes boron incorporation adjacent to π-systems even in substrates where the alkene is at a remote position, enabling a unique route to 1,1-diboron compounds from α -dienes.

Paramagnetic organometallic complexes. Synthesis of 17-electron cyclopentadienylcobalt complexes

The thermally stable 17-electron complexes [(η5-C5H5)CoL2] [BF4] (2; L = tertiary phosphines and phosphites) have been synthesized by one-electron oxidation of the corresponding 18-electron complexes,

Synthesis and reaction studies of phthaloylcobalt cations. Application to naphthoqulnone synthesis

Cationic phthaloylcabalt complesee 3-7 havt bwn pwpard by reaction of dtiorcobdh phtholoyl complex 1 with AgBF4 ffJlowwl by irauant with the appropriate ligimd. RtncUon of Lae cutionic cnraplwa wilh dkyns produced luphthoqulnuse, diid lh mecbanittic nature af ths results is diacuiwd. The cafionic cobalt complex 6 with a chelatmg diphoa bgand wai found to rapidly give high yields of nub Ututad naphthoquinonea on treatment with fuiicuonaliied alkynao in CH2Cl2.