1579298-18-2

Upstream product

• 350-51-6 3-fluorostyrene 
• 2561-17-3 1-ethynyl-3-fluoro-benzene 
• 74-95-3 1,1-dibromomethane 
• 455-36-7 1-(3-fluorophenyl)ethanone 

Downstream Products

• 1579298-05-7 1-(1-(3-fluorophenyl)vinyl)cyclobutanol 
• 1579298-24-0 (S)-2-(chloromethyl)-2-(3-fluorophenyl)cyclopentanone 
• 898752-08-4 ethyl 4-(3-fluorophenyl)-4-oxobutanoate 
• 219486-74-5 1-(buta-1,3-dien-2-yl)-3-fluorobenzene 

Relevant academic research and scientific papers

Synthesis of Macrocyclic Ketones through Catalyst-Free Electrophilic Halogen-Mediated Semipinacol Rearrangement: Application to the Total Synthesis of (±)-Muscone

A series of macrocycles were successfully prepared using electrophilic halogen-mediated semipinacol rearrangement under mild conditions. Although the expansion from small ring to medium ring is an energetically unfavorable process, the electrophilic halog

Synthesis of Unsymmetrical 1,4-Dicarbonyl Compounds by Photocatalytic Oxidative Radical Additions

Herein we report a photocatalytic oxidative radical addition reaction for the synthesis of unsymmetrical 1,4-dicarbonyl compounds. This reaction utilizes a desulfurization process to generate electrophilic radicals, which add to α-halogenated alkenes and undergo further oxidation to deliver 1,4-dicarbonyl compounds. This mild and highly efficient method provides a valuable alternative to known strategies.

Catalytic Asymmetric Halogenation/Semipinacol Rearrangement of 3-Hydroxyl-3-vinyl Oxindoles: A Stereodivergent Kinetic Resolution Process

A highly enantioselective halogenation/semipinacol rearrangement of isatin-derived allylic alcohols has been developed with a chiral N,N′-dioxide/ScIII complex as catalyst. This strategy involved a pivotal stereodivergent kinetic resolution process and provided a facile and efficient entry to optically active halo-substituted quinolone derivatives and quinoline alkaloids with a quaternary stereocenter simultaneously under mild reaction conditions. Based on the control experiments together with kinetic studies and DFT calculations, a possible catalytic cycle was proposed to illustrate the reaction process and enantiocontrol.

A Cascade Suzuki-Miyaura/Diels-Alder Protocol: Exploring the Bifunctional Utility of Vinyl Bpin

Cascade reactions are an important strategy in reaction design, allowing streamlining of chemical synthesis. Here we report a cascade Suzuki-Miyaura/Diels-Alder reaction, employing vinyl Bpin as a bifunctional reagent in two distinct roles: as an organoboron nucleo phile for cross-coupling and as a Diels-Alder dienophile. Merging these two reactions enables a rapid and operationally simple synthesis of functionalized carbocycles in good yield. The effect of the organoboron subtype on Diels-Alder regioselectivity was investigated and postsynthetic modifications were carried out on a model substrate. The potential for a complementary Heck/Diels-Alder process was also assessed.

Rh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols

We have developed a Rh(III)-catalyzed diastereoselective [2+1] annulation onto allylic alcohols initiated by alkenyl C-H activation of N-enoxyphthalimides to furnish substituted cyclopropyl-ketones. Notably, the traceless oxyphthalimide handle serves three functions: directing C-H activation, oxidation of Rh(III), and, collectively with the allylic alcohol, in directing cyclopropanation to control diastereoselectivity. Allylic alcohols are shown to be highly reactive olefin coupling partners leading to a directed diastereoselective cyclopropanation reaction, providing products not accessible by other routes.

Rh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols

We have developed a Rh(III)-catalyzed diastereoselective [2+1] annulation onto allylic alcohols initiated by alkenyl C-H activation of N-enoxyphthalimides to furnish substituted cyclopropyl-ketones. Notably, the traceless oxyphthalimide handle serves three functions: Directing C-H activation, oxidation of Rh(III), and, collectively with the allylic alcohol, in directing cyclopropanation to control diastereoselectivity. Allylic alcohols are shown to be highly reactive olefin coupling partners leading to a directed diastereoselective cyclopropanation reaction, providing products not accessible by other routes.

Rhodium(III)-Catalyzed Cyclopropanation of Unactivated Olefins Initiated by C-H Activation

We have developed a rhodium(III)-catalyzed cyclopropanation of unactivated olefins initiated by an alkenyl C-H activation. A variety of 1,1-disubstituted olefins undergo efficient cyclopropanation with a slight excess of alkene stoichiometry. A series of mechanistic interrogations implicate a metal carbene as an intermediate.

Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox-Catalyzed Ring Expansion

Azides are building blocks of increasing importance in synthetic chemistry, chemical biology, and materials science. Azidobenziodoxolone (ABX, Zhdankin reagent) is a valuable azide source, but its safety profile has not been thoroughly established. Herein, we report a safety study of ABX, which shows its hazardous nature. We introduce two derivatives, tBu-ABX and ABZ (azidobenziodazolone), with a better safety profile, and use them in established photoredox- and metal-mediated azidations, and in a new ring-expansion of silylated cyclobutanols to give azidated cyclopentanones.

Cyrene as a Bio-Based Solvent for the Suzuki-Miyaura Cross-Coupling

The Suzuki-Miyaura (SM) cross-coupling is the most broadly utilized Pd-catalyzed C-C bond-forming reaction in the chemical industry. A large proportion of SM couplings employ dipolar aprotic solvents; however, current sustainability initiatives and increasingly stringent regulations advocate the use of alternatives that exhibit more desirable properties. Here we describe the scope and utility of the bio-derived solvent Cyrene in SM cross-couplings and evaluate its suitability as a reaction medium for this benchmark transformation from discovery to gram scale.