Category: Dioxole

Nguyen, Qui-Hien published the artcileIntermolecular Palladium(0)-Catalyzed Atropo-enantioselective C-H Arylation of Heteroarenes, Name: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Journal of the American Chemical Society (2020), 142(5), 2161-2167, database is CAplus and MEDLINE.

Atropisomeric (hetero)biaryls are motifs with increasing significance in ligands, natural products, and biol. active mols. The straightforward construction of the stereogenic axis by efficient C-H functionalization methods is extremely rare and challenging. An intermol. and highly enantioselective C-H arylation of relevant heteroarenes providing an efficient access to atropisomeric (hetero)biaryls is reported. The use of a Pd(0) complex equipped with H₈-BINAPO as a chiral ligand enables the direct functionalization of a broad range of 1,2,3-triazoles and pyrazoles in excellent yields and selectivities of up to 97.5:2.5 er. The method also allows for an atroposelective double C-H arylation for the construction of two stereogenic axes with >99.5:0.5 er.

Journal of the American Chemical Society published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, Name: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Lin, Sen published the artcileCatalytic activities of dialkyltin compounds containing silicon to the condensation reaction of acetal (ketal)-alcohol, Quality Control of 177-10-6, the publication is Yingyong Huaxue (2013), 30(3), 271-275, database is CAplus.

The catalytic activities of ten dialkyltin compounds containing silicon were investigated through the condensation reaction of acetal (ketal)-alc. Factors such as amount of catalyst, reaction time, molar ratio of aldehyde (ketone) to alc. and solvent kind were studied toward the yield of reaction. The results show that, except one catalyst, nine compounds are good in catalytic activities for the acetalization and ketalization. The yield reached 92% and 86% under optimal compounds: catalyst dosage was 1.4% based on the mass of the reactants, the molar ratio of the aldehyde to glycol was 1:1.3, ketone to glycol was 1:1.9, cyclohexane was used as the water carrying agent, and the reaction was refluxed for 3 h.

Yingyong Huaxue published new progress about 177-10-6. 177-10-6 belongs to dioxole, auxiliary class Dioxolane,Spiro, name is 1,4-Dioxaspiro[4.5]decane, and the molecular formula is C8H14O2, Quality Control of 177-10-6.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Xu, Xiaofeng published the artcile2,7-Carbazole-1,4-phenylene Copolymers with Polar Side Chains for Cathode Modifications in Polymer Light-Emitting Diodes, Safety of 9-(6-Bromohexyl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, the publication is Macromolecules (Washington, DC, United States) (2011), 44(11), 4204-4212, database is CAplus.

Alc.-soluble 2,7-carbazole-1,4-phenylene copolymers PCP-NOH and PCP-EP, comprising surfactant-like diethanolamino and phosphonate end groups on the side chains, resp., were synthesized and utilized as electron injection layer (EIL) in combination with high work function Al electrode in polymer light-emitting diodes (PLEDs). The UV-vis absorption and photoluminescence properties of the PCP-NOH and PCP-EP are mainly determined by the conjugated 2,7-carbazole-1,4-phenylene main chain. The PCP-NOH and PCP-EP possess comparable HOMO levels of -5.20 eV and LUMO levels around -2.35 eV. Multilayer PLEDs with a device configuration of ITO/PEDOT:PSS (40 nm)/emissive layer (70 nm)/EIL (15 nm)/Al (100 nm) were successfully fabricated. With fluorescent PFO-DBT15 as the emissive layer, the PLEDs using the PCP-NOH and PCP-EP as the EIL displayed luminous efficiency (LE) of 1.01 and 0.88 cd/A, resp., all obviously higher than 0.015 cd/A for sole Al cathode and 0.58 cd/A for the well-known Ba/Al cathode. With a phosphorescent Ir(mppy)₃-doped polymer blend (PVK:PBD:Ir(mppy)₃ = 100:30:1) as the emissive layer, the PLEDs with the EIL showed high maximum LE of 39.3 cd/A for PCP-NOH and 42.5 cd/A for PCP-EP, in comparison to 0.35 cd/A for sole Al cathode and 32.2 cd/A for the Ba/Al cathode. Particularly, the PLED with PCP-EP as EIL exhibited an excellent LE of 33.3 cd/A at a c.d. of 61.1 mA/cm² (luminance = 20 300 cd/cm²), showing weak roll-off of efficiency at high c.d. Inserting the polar alc.-soluble polymers as interlayer can significantly increase built-in potentials in the PLEDs, from which electron injection barrier from the Al electrode is decreased. The results indicate that the PCP-NOH and PCP-EP are excellent electron injection polymers for high-performance PLEDs with high work function Al electrode.

Macromolecules (Washington, DC, United States) published new progress about 1268162-40-8. 1268162-40-8 belongs to dioxole, auxiliary class Boronic acid and ester,Boronic acid and ester,Bromide, name is 9-(6-Bromohexyl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, and the molecular formula is C14H22BNO4S, Safety of 9-(6-Bromohexyl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Mita, Tsuyoshi published the artcileCo-Catalyzed Direct Addition of Allylic C(sp³)-H Bonds to Ketones, Computed Properties of 503538-69-0, the publication is Organic Letters (2017), 19(21), 5876-5879, database is CAplus and MEDLINE.

By using Co(acac)₂/Xantphos with AlMe₃, the C(sp³)-H bonds of allylarene derivatives were cleaved for reaction with various ketones, affording the homoallylic alcs. in moderate to good yields. The branch/linear selectivity depended on the steric and electronic factors of the ketone electrophiles. The intermediate in this reaction is thought to be a low-valent allylcobalt(I) species, which exhibits high nucleophilicity toward ketones.

Organic Letters published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, Computed Properties of 503538-69-0.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Yang, Zhi-Wang published the artcileBaeyer-Villiger oxidation and acetalization of cyclic ketones on SO^2-₄/SnO₂-Fe₂O₃ solid acid catalysts, Formula: C8H14O2, the publication is Wuli Huaxue Xuebao (2012), 28(9), 2148-2154, database is CAplus.

Fe-doped SO^2-₄/SnO₂ (STF) solid acid catalysts with different amounts of iron were prepared via co-condensation, followed by sulfation and calcination. These materials were characterized by Fourier transform IR (FTIR) spectroscopy, x-ray powder diffraction (XRD), N₂ adsorption-desorption anal. (BET), thermogravimetric (TG) anal., and SEM. The Fe-doped catalysts exhibited more activity than undoped catalysts in acetalization reactions of 4-tert-butylcyclohexanone and diols. The catalytic acetalization of several ketones and 1,2-diols with the SO^2-₄/SnO₂-Fe₂O₃ catalysts (with the Fe/Sn molar ratio of 0.5) were studied. The influence of the reaction time and the amount of the catalysts on the acetalization were also investigated. In addition, the high performance of this Fe-modified catalyst was demonstrated in the Baeyer-Villiger oxidation of cyclic ketones. The catalyst can be recycled several times without any significant loss in catalytic activity.

Wuli Huaxue Xuebao published new progress about 177-10-6. 177-10-6 belongs to dioxole, auxiliary class Dioxolane,Spiro, name is 1,4-Dioxaspiro[4.5]decane, and the molecular formula is C12H23N3S, Formula: C8H14O2.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Ye, Zhi-Shi published the artcileIridium-catalyzed asymmetric hydrogenation of pyridinium salts, Application of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Angewandte Chemie, International Edition (2012), 51(40), 10181-10184, S10181/1-S10181/62, database is CAplus and MEDLINE.

A highly efficient iridium-catalyzed asym. hydrogenation of 2-substituted pyridinium salts is developed. A series of chiral 2-substituted piperidines were obtained in good to excellent yields and up to 93% ee.

Angewandte Chemie, International Edition published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C9H22OSi, Application of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Chan, Vincent S. published the artcileDevelopment of ruthenium catalysts for the enantioselective synthesis of P-stereogenic phosphines via nucleophilic phosphido intermediates, Safety of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, the publication is Journal of the American Chemical Society (2009), 131(16), 6021-6032, database is CAplus and MEDLINE.

Ruthenium chiral diphosphine complexes [L₂RuH][BPh₄] or [(L¹)(dmpe)RuH][BPh₄] [L, L¹ = chiral diphosphines, dmpe = 1,2-bis(dimethylphosphino)ethane] catalyze base-promoted low-temperature asym. alkylation of secondary phosphine PhMePH by benzyl halides, yielding chiral PhMe(ArCH₂)P (Ar = Ph, 4-ClC₆H₄, 4-MeC₆H₄, 4-MeOC₆H₄, 2-MeC₆H₄, 1-naphthyl, 2-pyridinyl, 2-furanyl) or diphosphines PhMePCH₂Ar¹CH₂PMePh (Ar¹ = 1,3-phenylene, 1,2-phenylene, 1,3-pyridinediyl) with up to 80% ee [L = 4-ⁱPr-2-(C₆H₄PPh₂-2)oxazoline (ⁱPr-PHOX) or L¹ = MeO-BiPHEP, SEGPHOS]. The optimized base for the reaction was found to be sodium tert-amylate, which prevents the occurrence of background non-catalytic alkylation by deprotonation of uncoordinated PhMePH. The reactions proceed through the intermediacy of nucleophilic phosphido species, which have low barriers to pyramidal inversion; this allows for a dynamic kinetic asym. alkylation. The initially discovered [((R)-ⁱPr-PHOX)₂Ru(H)][BPh₄] (6) catalyst was found to be effective in the reaction with benzylic chlorides; moreover, the alkylation displayed an unusual temperature dependence. However, the limited scope of alkylation of 6 motivated further studies which led to the development of two complementary chiral mixed ligand Ru(II) catalysts of type [L¹L²Ru(H)]⁺. These catalysts were derived from a combination of one chiral and one achiral ligand, where a synergistic interaction of the two ligands creates an effective asym. environment around the ruthenium center. The (R)-MeO-BiPHEP catalyst [((R)-MeO-BiPHEP)(dmpe)RuH][BPh₄] (10) was found to be effective for the asym. alkylation by benzyl chlorides, while the (R)-DIFLUORPHOS catalyst [[(R)-DIFLUORPHOS](dmpe)RuH][BPh₄] (11) was optimal for the nucleophilic substitution of less activated alkyl bromides; the scope of the resp. catalysts was also explored.

Journal of the American Chemical Society published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C38H24F4O4P2, Safety of (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Lin, Junzhong published the artcileHierarchical Shell-Like ZSM-5 with Tunable Porosity Synthesized by using a Dissolution-Recrystallization Approach, Quality Control of 177-10-6, the publication is Chemistry – A European Journal (2018), 24(56), 14974-14981, database is CAplus and MEDLINE.

Zeolites have been widely used in various fields in industry, such as catalysis, separation, and adsorption, etc. The small pore size of the micropores in the zeolite could lead to severe diffusion resistance in mass transfer. Numerous efforts have been dedicated to imposing hierarchical pore systems into zeolites by using templates or leaching methods. Here, we report the synthesis of single-crystalline hierarchical shell-like ZSM-5 by utilizing a dissolution-recrystallization post-treatment on mesoporous ZSM-5. Tetrapropylammonium hydroxide solution was used in the post-treatment. The hierarchical porosity in the crystalline shell can be controlled by adding sodium cations into the synthesis system. The hierarchical shell-like ZSM-5 reported here shows higher catalytic activity in acetalization reactions containing bulky mols.

Chemistry – A European Journal published new progress about 177-10-6. 177-10-6 belongs to dioxole, auxiliary class Dioxolane,Spiro, name is 1,4-Dioxaspiro[4.5]decane, and the molecular formula is C8H14O2, Quality Control of 177-10-6.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Climent, Maria Jose published the artcileSynthesis of hyacinth, vanilla, and blossom orange fragrances: the benefit of using zeolites and delaminated zeolites as catalysts, Recommanded Product: 2-Methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol, the publication is Applied Catalysis, A: General (2004), 263(2), 155-161, database is CAplus.

The synthesis of phenylacetaldehyde glycerol acetals, 2-benzyl-4-hydroxymethyl-1,3-dioxolane (1), 2-benzyl-5-hydroxy-1,3-dioxane (2), and vanillin propylene glycol acetal (2-(4-hydroxy-3-methoxyphenyl)-4-methyl-1,3-dioxolane) (3) which are flavoring compounds with hyacinth and vanilla scent fragrances, have been carried out successfully by acetalization of phenylacetaldehyde and vanillin with glycerol and propylene glycol, resp., using toluene as solvent and zeolite catalysts whose adsorption properties have been optimized. However, in the case of a larger size acetal such as 2-acetonaphthone propylene glycol acetal (4) with blossom orange scent, geometrical constraints make the diffusion of reactants and products inside the micropores more difficult. In this case, a delaminated zeolite (ITQ-2) with very large and structured external surface is an active and selective catalyst. Furthermore, the delaminated zeolite allows the reaction to be carried out in a solvent-free system, opening the possibility for an environmentally friendly process for the synthesis of acetal fragrances.

Applied Catalysis, A: General published new progress about 68527-74-2. 68527-74-2 belongs to dioxole, auxiliary class Dioxolane,Benzene,Phenol,Ether, name is 2-Methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol, and the molecular formula is C11H14O4, Recommanded Product: 2-Methoxy-4-(4-methyl-1,3-dioxolan-2-yl)phenol.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem

Seiser, Tobias published the artcileRhodium(I)-Catalyzed 1,4-Silicon Shift of Unactivated Silanes from Aryl to Alkyl: Enantioselective Synthesis of Indanol Derivatives, Computed Properties of 503538-69-0, the publication is Angewandte Chemie, International Edition (2010), 49(52), 10163-10167, S10163/1-S10163/55, database is CAplus and MEDLINE.

Enantioselective Rh-promoted activation and 1,4-positional swap of unactivated tetraorganosilanes, e.g., 1-ethyl-3-methyl-3-(2-(trimethylsilyl)phenyl)cyclobutanol (I) to give (1S,3S)-1-ethyl-3-methyl-3((trimethylsilyl)methyl)indanol (II). E.g., reaction of silylphenyl tert-cyclobutanol I with 2.5 mol% [Rh(cod)OH]₂/6.0 mol% (R)-Difluorphos ligand at 100° in mesitylene gave 82% yield of trans-indanol II (97% ee).

Angewandte Chemie, International Edition published new progress about 503538-69-0. 503538-69-0 belongs to dioxole, auxiliary class (Atropisomeric Bisphosphine Ligands, name is (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, and the molecular formula is C12H17BO4S, Computed Properties of 503538-69-0.

Referemce:
https://en.wikipedia.org/wiki/1,3-Benzodioxole,
Dioxole | C3H4O2 – PubChem