59142-67-5

Upstream product

• 6630-33-7 ortho-bromobenzaldehyde 
• 352-13-6 4-flourophenylmagnesium bromide 
• 1765-93-1 4-fluoroboronic acid 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 540-36-3 para-difluorobenzene 

Downstream Products

• 60081-08-5 1-bromo-2-[(4-fluoro-phenyl)-methoxy-methyl]-benzene 
• 60081-24-5 1'-benzyl-3-(4-fluoro-phenyl)-3H-spiro[isobenzofuran-1,4'-piperidine] 
• 1514-15-4 3-fluoro-9-fluorenone 
• 573-46-6 (2-bromophenyl)(4-fluorophenyl)methanone 
• 1379674-98-2 C₁₈H₁₉FSi 
• 1379674-57-3 1-ethynyl-2-(4-fluorobenzyl) benzene 
• 85662-85-7 3-(4-fluorophenyl)-2,3-dihydro-1H-indene-1-one 
• 68355-79-3 1-bromo-2-(4-fluorobenzyl)benzene 
• 343-40-8 3-fluoro-9H-fluorene 

Relevant academic research and scientific papers

Divergent Access to Benzocycles through Copper-Catalyzed Borylative Cyclizations

A copper-catalyzed chemodivergent approach to five- and six-membered benzocycles from dienyl arenes tethered with a ketone has been developed. Through proper choice of coordinating ligands and catalytic conditions, copper-catalyzed borylative cyclization of a single dienyl arene can be diverted to two different pathways, leading to indanols and dihydronaphthalenols with high stereoselectivity. The chiral bidentate bisphosphine ligand (S,S)-Ph-BPE was optimal for asymmetric copper-allyl addition to a tethered ketone via a boat-like transition state, whereas NHC ligands led to boro-allyl addition producing indanols with high diastereoselectivity. (Figure presented.).

SUBSTITUTED NAPHTHYRIDINONE COMPOUNDS USEFUL AS T CELL ACTIVATORS

Disclosed are compounds of Formula (I) or a salt thereof, wherein: R1, R2, R3, R4, R5, and m are defined herein. Also disclosed are methods of using such compounds to inhibit the activity of one or both of diacylglycerol kinase alpha (DGKα) and diacylglycerol kinase zeta (DGKζ), and pharmaceutical compositions comprising such compounds. These compounds are useful in the treatment of viral infections and proliferative disorders, such as cancer.

Asymmetric Synthesis of 1,2-Dihydronaphthalene-1-ols via Copper-Catalyzed Intramolecular Reductive Cyclization

We describe a copper-catalyzed intramolecular reductive cyclization of easily accessible benz-tethered 1,3-dienes containing a ketone moiety. This process provided biologically active 1,2-dihydronaphthalene-1-ol derivatives in good yields with excellent enantio- and diastereoselectivity. Mechanistic investigations using density functional theory revealed that (Z)- and (E)-allylcopper intermediates formed in situ from the diene and copper catalyst undergo isomerization and selective intramolecular allylation of the (E)-allylcopper form of the major product through a six-membered boatlike transition state. The resulting products were further transformed to fully saturated naphthalene-1-ols by reactions of the olefin moiety.

Chiral electron-rich PNP ligand with a phospholane motif: Structural features and application in asymmetric hydrogenation

Despite the remarkable reactivity that was achieved by a series of transition-metal catalysts with a PNP type ligand, the electron-rich chiral PNP ligands have still been rarely reported because of the difficulties in synthesis and the nature of air-sensitivity. Herein, we report a novel chiral PNP ligand (Heng-PNP) with both a rigid backbone and a bulky tert-butyl group on the phospholane motif. We successfully obtained its divalent iron complex. The chiral environment of its Ir(III) complex was also discussed with quadrant analysis. This tridentate ligand was applied in iridium-catalyzed asymmetric hydrogenation of challenging diaryl ketones: up to 98% ee and 500 TON are achieved. Computational study showed that the twist of conjugate aryl group in the substrate (induced by the special chiral pocket of Ir/Heng-PNP complex) leads to the energy difference in the enantiodetermining step.

Efficient palladium-catalyzed C(sp2)-H activation towards the synthesis of fluorenes

A facile protocol for the synthesis of fluorene derivatives has been developed through palladium-catalyzed cyclization of 2′-halo-diarylmethanes via activation of arylic C-H bonds. The reactions occurred smoothly and allowed both electron-rich and electron-deficient substrates to convert into their corresponding fluorenes in good to excellent yields. Studies revealed that this Pd-catalyzed cyclization was also available for the substrates of 2′-chloro-diarylmethanes and no catalyst poisoning occurred for 2′-iodo-diphenylmethane.

Borylation of Olefin C-H Bond via Aryl to Vinyl Palladium 1,4-Migration

The aryl to vinyl palladium 1,4-migration was realized for the first time. The generated alkenyl palladium species was trapped by diboron reagents under Miyaura borylation conditions, providing a new method to synthesize β,β-disubstituted vinylboronates. The excellent regioselectivity and broad substrate scope were observed for this novel transformation.

Bismuth-catalyzed synthesis of anthracenes via cycloisomerization of o-alkynyldiarylmethane

In this study, anthracenes were efficiently synthesized from o-alkynyldiarylmethane using a novel method that exploits the synergistic effect between Bi(OTf)3 as the catalyst, and trifluoroacetic acid (TFA). Through this reaction, we achieved the rapid and efficient synthesis of anthracenes bearing various functional groups under mild conditions.

Flexible and practical synthesis of anthracenes through gold-catalyzed cyclization of o -alkynyldiarylmethanes

A concise gold-catalyzed method for the preparation of anthracenes from o-alkynyldiarylmethanes has been developed. Under mild reaction conditions, versatile anthracene derivatives were formed in moderate to good yields. The high flexibility, broad substrate scope, and mild nature of this reaction render it a viable alternative for the synthesis of anthracenes.

Gold-catalyzed oxidative cyclizations of cis-3-En-1-ynes to form cyclopentenone derivatives

Golden tendencies: The title reaction for synthesizing cyclopentenone derivatives utilizes a gold complex and 8-methylquinoline oxide as the catalyst system (see scheme; IPr=1,3-bis(diisopropylphenyl)imidazol-2-ylidene). Such products are not attainable using diazocarbonyl reagents, as the gold carbenoids tend to react with C-H bonds. Copyright

Practical radical cyclizations with arylboronic acids and trifluoroborates

Practical radical cyclizations using organoboronic acids and trifluoroborates take place in water, open to air, and in a scalable fashion employing catalytic silver nitrate and stoichiometric potassium persulfate. Both Pschorr-type cyclizations and tandem radical cyclization/trap cascades are described, illustrating the utility of these mild conditions for the generation of polycyclic scaffolds.