Category: 53731-26-3

Hori, Kaishi published the artcilePrecatalyst Effects on Pd-Catalyzed Cross-Coupling Difluoromethylation of Aryl Boronic Acids, Category: naphthyridine, the publication is ACS Catalysis (2019), 9(1), 417-421, database is CAplus.

The Pd-catalyzed difluoromethylation of aryl boronic acids with difluoroiodomethane is shown to provide the difluoromethyl compounds I (R = H, 4-Ph, 3-MeO, 2-NH₂, etc.) in high to moderate yields by Pd(PPh₃)₂/DPEphos catalyst in H₂O/toluene. Mechanistic studies show that the oxidative addition by Pd(PPh₃)₄ rather than Pd₂(dba)₃ precatalyst to difluoroiodomethane provides a square-planar trans-(PPh₃)₂Pd(II)(CF₂H)I complex defined by X-ray crystallog. anal. The trans-(PPh₃)₂Pd(CF₂H)I complex is transformed to cis-(PPh₃)₂Pd(CF₂H)Ph detected by low temperature NMR anal., via transmetalation with phenylboronic acids. The reductive elimination occurs via ligand exchange to DPEphosPd(CF₂H)Ph to give Ph-CF₂H (t_1/2 = 144.7 min at 20 °C) with formation of the Pd(0)(PPh₃)₂/DPEphos catalyst.

ACS Catalysis published new progress about 53731-26-3. 53731-26-3 belongs to naphthyridine, auxiliary class Difluoromethyl,Fluoride,Naphthalene, name is 1-(Difluoromethyl)naphthalene, and the molecular formula is C11H8F2, Category: naphthyridine.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Yoshida, Masato published the artcileConvenient preparation of (chlorodifluoromethyl)arenes. Useful precursors for aryldifluoromethyl radicals, Safety of 1-(Difluoromethyl)naphthalene, the publication is Chemistry Letters (1992), 227-30, database is CAplus.

The chlorodifluoromethyl group was introduced into aromatic rings (of e.g., C₆H₆ to give PhCF₂Cl) using bis(chlorodifluoroacetyl) peroxide which was readily prepared from the corresponding acid anhydride with 30% hydrogen peroxide, and the chlorine was successively replaced by hydrogen or the allyl group in excellent yields under radical conditions.

Chemistry Letters published new progress about 53731-26-3. 53731-26-3 belongs to naphthyridine, auxiliary class Difluoromethyl,Fluoride,Naphthalene, name is 1-(Difluoromethyl)naphthalene, and the molecular formula is C18H17N5O3, Safety of 1-(Difluoromethyl)naphthalene.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Yoshida, Masato published the artcileConvenient preparation of difluoromethylene-functionalized compounds from chlorodifluoroacetic acid, Safety of 1-(Difluoromethyl)naphthalene, the publication is Journal of Fluorine Chemistry (1994), 68(1), 33-8, database is CAplus.

A convenient route for the synthesis of difluoromethylene-functionalized compounds from chlorodifluoroacetic acid has been investigated. Bis(chlorodifluoroacetyl) peroxide, which was synthesized from chlorodifluoroacetic acid via its acid anhydride, was found to be a good reagent for the chlorodifluoromethylation of electron-rich aromatic compounds and olefins. The chlorine atom of the chlorodifluoromethylated compounds, thus prepared, exchanged hydrogen and allyl groups by reaction with tributyltin hydride and allyltributyltin, resp., under radical conditions.

Journal of Fluorine Chemistry published new progress about 53731-26-3. 53731-26-3 belongs to naphthyridine, auxiliary class Difluoromethyl,Fluoride,Naphthalene, name is 1-(Difluoromethyl)naphthalene, and the molecular formula is C8H11NO, Safety of 1-(Difluoromethyl)naphthalene.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Hara, Shoji published the artcileIF₅-pyridine-HF: air- and moisture-stable fluorination reagent, Quality Control of 53731-26-3, the publication is Tetrahedron (2012), 68(49), 10145-10150, database is CAplus.

IF₅-pyridine-HF, an air- and moisture-stable solid, can be used as a fluorination reagent for the introduction of fluorine atoms to the α-position of the sulfur atom in sulfides. The desulfurizing-fluorination reactions of benzylic sulfides, thioacetals, and 2-(methylthio)-1,3-dithiane derivatives were also performed using this reagent.

Tetrahedron published new progress about 53731-26-3. 53731-26-3 belongs to naphthyridine, auxiliary class Difluoromethyl,Fluoride,Naphthalene, name is 1-(Difluoromethyl)naphthalene, and the molecular formula is C11H8F2, Quality Control of 53731-26-3.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Feng, Zhang published the artcileAccess to Difluoromethylated Arenes by Pd-Catalyzed Reaction of Arylboronic Acids with Bromodifluoroacetate, Recommanded Product: 1-(Difluoromethyl)naphthalene, the publication is Organic Letters (2016), 18(1), 44-47, database is CAplus and MEDLINE.

An unprecedented example of Pd-catalyzed difluoromethylation of aryl boronic acids with bromodifluoroacetate is described. The reaction proceeds under mild reaction conditions with hydroquinone and Fe(acac)₃ as additives. Preliminary mechanistic studies reveal that a difluorocarbene pathway is involved in the reaction, which is unusual compared to the most traditional approaches. This reaction has advantages of high efficiency and excellent functional group compatibility, even toward bromide and hydroxy group, thus providing a useful protocol for drug discovery and development.

Organic Letters published new progress about 53731-26-3. 53731-26-3 belongs to naphthyridine, auxiliary class Difluoromethyl,Fluoride,Naphthalene, name is 1-(Difluoromethyl)naphthalene, and the molecular formula is C11H8F2, Recommanded Product: 1-(Difluoromethyl)naphthalene.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Feng, Zhang published the artcileChlorodifluoromethane-triggered formation of difluoromethylated arenes catalysed by palladium, Product Details of C11H8F2, the publication is Nature Chemistry (2017), 9(9), 918-923, database is CAplus and MEDLINE.

Difluoromethylated aromatic compounds are of increasing importance in pharmaceuticals, agrochems. and materials. Chlorodifluoromethane (ClCF₂H), an inexpensive, abundant and widely used industrial raw material, represents the ideal and most straightforward difluoromethylating reagent, but introduction of the difluoromethyl group (CF₂H) from ClCF₂H into aromatics has not been reported. Here, we describe a direct palladium-catalyzed difluoromethylation method for coupling ClCF₂H with arylboronic acids and esters to generate difluoromethylated arenes with high efficiency. The reaction exhibits a remarkably broad substrate scope, including heteroarylboronic acids, and was used for difluoromethylation of a range of pharmaceuticals and biol. active compounds Preliminary mechanistic studies revealed that a palladium difluorocarbene intermediate is involved in the reaction. Although numerous metal-difluorocarbene complexes were prepared, the catalytic synthesis of difluoromethylated or difluoromethylenated compounds involving metal-difluorocarbene complexes has not received much attention. This new reaction therefore also opens the door to understand metal-difluorocarbene complex catalyzed reactions.

Nature Chemistry published new progress about 53731-26-3. 53731-26-3 belongs to naphthyridine, auxiliary class Difluoromethyl,Fluoride,Naphthalene, name is 1-(Difluoromethyl)naphthalene, and the molecular formula is C11H8F2, Product Details of C11H8F2.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Motohashi, Hirotaka published the artcileNickel-Catalyzed Aromatic Cross-Coupling Difluoromethylation of Grignard Reagents with Difluoroiodomethane, Quality Control of 53731-26-3, the publication is Organic Letters (2018), 20(17), 5340-5343, database is CAplus and MEDLINE.

The nickel-catalyzed cross-coupling difluoromethylation of the Grignard reagents with difluoroiodomethane is shown to provide the corresponding aromatic difluoromethyl products in excellent to moderate yields. The difluoromethylation proceeds smoothly within 1 h at room temperature with 1.5 equiv of the Grignard reagents in the presence of Ni(cod)₂/TMEDA (2.5-0.5 mol %). Mechanistic studies clarify that the oxidative addition of the Ni(0) catalyst to difluoroiodomethane provides the TMEDA-Ni(II)(CF₂H)I complex. This intermediate is transformed to TMEDA-Ni(II)(CF₂H)Ph via transmetalation with PhMgBr. The reductive elimination takes place to give the aromatic cross-coupling difluoromethylation product along with regeneration of the TMEDA-Ni(0) catalyst. ESR (EPR) and radical clock analyses of the nickel-catalyzed reaction provide no EPR active Ni(I) and Ni(III) species at around g = 2 and only a trace amount of the cyclization product.

Organic Letters published new progress about 53731-26-3. 53731-26-3 belongs to naphthyridine, auxiliary class Difluoromethyl,Fluoride,Naphthalene, name is 1-(Difluoromethyl)naphthalene, and the molecular formula is C11H8F2, Quality Control of 53731-26-3.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Gu, Yang published the artcileCooperative dual palladium/silver catalyst for direct difluoromethylation of aryl bromides and iodides, COA of Formula: C11H8F2, the publication is Nature Communications (2014), 5405, database is CAplus and MEDLINE.

A cooperative dual palladium/silver catalyst system for direct difluoromethylation of aryl bromides and iodides under mild conditions is reported. The system is developed by initial preparation of the putative intermediates in the dual-catalytic cycles, followed by studying the elemental steps to demonstrate the viability of the proposed cooperative catalytic cycle. The reaction is compatible with a variety of functional groups such as ester, amide, protected phenoxide, protected ketone, cyclopropyl, bromide, and heteroaryl subunits such as pyrrole, benzothiazole, carbazole or pyridine.

Nature Communications published new progress about 53731-26-3. 53731-26-3 belongs to naphthyridine, auxiliary class Difluoromethyl,Fluoride,Naphthalene, name is 1-(Difluoromethyl)naphthalene, and the molecular formula is C11H8F2, COA of Formula: C11H8F2.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Motohashi, Hirotaka published the artcileLigand-Less Iron-Catalyzed Aromatic Cross-Coupling Difluoromethylation of Grignard Reagents with Difluoroiodomethane, Recommanded Product: 1-(Difluoromethyl)naphthalene, the publication is Journal of Organic Chemistry (2019), 84(10), 6483-6490, database is CAplus and MEDLINE.

Iron-catalyzed cross-coupling difluoromethylations of the Grignard reagents with difluoroiodomethane provide various aromatic difluoromethyl products in good yields, not employing sterically demanding ligands. Difluoromethylations proceed within 30 min at -20 °C with 2.0 equiv of the Grignard reagents and FeCl₃ or Fe(acac)₃ (2.5 mol %). Mechanistic investigations clarify difluoromethyl radical intervention; Fe(0) ate is initially generated. Single electron transfer from Fe(0) ate to difluoroiodomethane takes place. Recombination with aryl groups gives Ar-CF₂Hs. The catalyst can be regenerated by the Grignard reagents.

Journal of Organic Chemistry published new progress about 53731-26-3. 53731-26-3 belongs to naphthyridine, auxiliary class Difluoromethyl,Fluoride,Naphthalene, name is 1-(Difluoromethyl)naphthalene, and the molecular formula is C11H8F2, Recommanded Product: 1-(Difluoromethyl)naphthalene.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem