312693-23-5

Usage

Uses

Used in Organic Synthesis:
2-METHYLPHENYLZINC IODIDE is used as a reagent for forming carbon-carbon bonds through cross-coupling reactions. It is instrumental in the synthesis of complex organic molecules due to its compatibility with a range of electrophiles, such as alkyl, aryl, and vinyl halides.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-METHYLPHENYLZINC IODIDE is utilized as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to form carbon-carbon bonds with different electrophiles allows for the creation of diverse molecular structures, which can be further developed into potential drug candidates.
Used in Material Science:
2-METHYLPHENYLZINC IODIDE is also used in material science as a precursor for the development of new materials with specific properties. Its role in forming carbon-carbon bonds can contribute to the synthesis of novel polymers, composites, and other materials with tailored characteristics for various applications.
Used in Research and Development:
In the field of research and development, 2-METHYLPHENYLZINC IODIDE serves as a versatile tool for exploring new chemical reactions and mechanisms. Its reactivity with various electrophiles provides a platform for studying the formation of carbon-carbon bonds and the development of innovative synthetic methodologies.

InChI:InChI=1/C7H7.HI.Zn/c1-7-5-3-2-4-6-7;;/h2-5H,1H3;1H;/q;;+1/p-1/rC7H7IZn/c1-6-4-2-3-5-7(6)9-8/h2-5H,1H3

Upstream product

• 615-37-2 ortho-methylphenyl iodide 
• 7440-66-6 zinc 

Downstream Products

• 1280725-50-9 (R)-4-phenyl-4-(o-tolyl)butan-2-one 
• 1504589-18-7 tert-butyl 2-(o-tolylsulfonyl)acetate 

Relevant academic research and scientific papers

Enantioselective Conjugate Addition of Stabilized Arylzinc Iodide to Enones: an Improved Protocol of the Hayashi Reaction

Stabilised arylzinc iodide, prepared by direct insertion of zinc into aryl iodides, were used as nucleophiles in the Hayashi Rh-catalysed enantioselective conjugate addition to enones. The reaction conditions were optimized in the addition of phenylzinc i

Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ,γ-Diarylcarbonyl and Aryltetralone Derivatives

We report a Ni-catalyzed regioselective α-carbonylalkylarylation of vinylarenes with α-halocarbonyl compounds and arylzinc reagents. The reaction works with primary, secondary, and tertiary α-halocarbonyl molecules, and electronically varied arylzinc reagents. The reaction generates γ,γ-diarylcarbonyl derivatives with α-secondary, tertiary, and quaternary carbon centers. The products can be readily converted to aryltetralones, including a precursor to Zoloft, an antidepressant drug.

Arylzinc Halides by Silver Catalyzed Zinc Insertion into Aryl Iodides

A catalytic amount of silver acetate efficiently promotes direct insertion of zinc metal into aryl iodides, having different structure, in ethereal solvent. Electron-rich substrates also rapidly undergo oxidative metalation. The arylzinc iodides formed give Negishi coupling products under mild reaction conditions to obtain biaryls in high yields. Sensitive functional groups like aldehydes and primary amides are well-tolerated.

Ni-Catalyzed Regioselective Alkylarylation of Vinylarenes via C(sp3)-C(sp3)/C(sp3)-C(sp2) Bond Formation and Mechanistic Studies

We report a Ni-catalyzed regioselective alkylarylation of vinylarenes with alkyl halides and arylzinc reagents to generate 1,1-diarylalkanes. The reaction proceeds well with primary, secondary and tertiary alkyl halides, and electronically diverse arylzinc reagents. Mechanistic investigations by radical probes, competition studies and quantitative kinetics reveal that the current reaction proceeds via a Ni(0)/Ni(I)/Ni(II) catalytic cycle by a rate-limiting direct halogen atom abstraction via single electron transfer to alkyl halides by a Ni(0)-catalyst.

Ni-Catalyzed Regioselective Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling and Application to the Concise Synthesis of Lignan Natural Products

We disclose a (terpy)NiBr2-catalyzed reaction protocol that regioselectively difunctionalizes unactivated olefins with tethered alkyl halides and arylzinc reagents. The reaction shows an excellent functional group tolerance (such as ketones, es