Tag: M.W=400-450

Goutierre, Anne-Sophie’s team published research in Organometallics in 36 | CAS: 1160556-64-8

Organometallics published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Application In Synthesis of 1160556-64-8.

Goutierre, Anne-Sophie published the artcileComparative structural analysis of biarylphosphine ligands in arylpalladium bromide and malonate complexes, Application In Synthesis of 1160556-64-8, the publication is Organometallics (2017), 36(1), 129-135, database is CAplus.

The substitution of biarylphosphine ligands was shown to have a marked impact on the α/β selectivity of the arylation of ester enolates. To get further insight into this effect, the solid-state structures of arylpalladium bromide and malonate complexes [(R3P)Pd(ArF)Br]2 and [(R3P)Pd(ArF)[O:C(OMe)CHC(OMe):O]] [ArF = 3,5-(CF3)2C6H3] with four different biarylphosphine ligands were obtained by X-ray diffraction anal. Structural differences were not very pronounced except for the conformationally restricted CPhos ligand, which showed a bidentate coordination mode in the oxidative addition complex, whereas the other ligands form dimeric species.

Organometallics published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Application In Synthesis of 1160556-64-8.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

 

Newman-Stonebraker, Samuel H.’s team published research in Science (Washington, DC, United States) in 374 | CAS: 1160556-64-8

Science (Washington, DC, United States) published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Recommanded Product: 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine.

Newman-Stonebraker, Samuel H. published the artcileUnivariate classification of phosphine ligation state and reactivity in cross-coupling catalysis, Recommanded Product: 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, the publication is Science (Washington, DC, United States) (2021), 374(6565), 301-308, database is CAplus and MEDLINE.

Minimal buried volume of the phosphine ligands was correlated with the stoichiometry of nickel and palladium complexes and catalytic activity in Suzuki, Heck and Buchwald amination reactions. Chemists often use statistical anal. of reaction data with mol. descriptors to identify structure-reactivity relationships, which can enable prediction and mechanistic understanding. In this study, we developed a broadly applicable and quant. classification workflow that identifies reactivity cliffs in 11 Ni- and Pd-catalyzed cross-coupling datasets using monodentate phosphine ligands. A distinctive ligand steric descriptor, min. percent buried volume [%Vbur (min)], is found to divide these datasets into active and inactive regions at a similar threshold value. Organometallic studies demonstrate that this threshold corresponds to the binary outcome of bisligated vs. monoligated metal and that %Vbur (min) is a phys. meaningful and predictive representation of ligand structure in catalysis.

Science (Washington, DC, United States) published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Recommanded Product: 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

 

DeBergh, J. Robb’s team published research in Journal of the American Chemical Society in 135 | CAS: 1160556-64-8

Journal of the American Chemical Society published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Formula: C28H41N2P.

DeBergh, J. Robb published the artcileSynthesis of Aryl Sulfonamides via Palladium-Catalyzed Chlorosulfonylation of Arylboronic Acids, Formula: C28H41N2P, the publication is Journal of the American Chemical Society (2013), 135(29), 10638-10641, database is CAplus and MEDLINE.

A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions. E.g., in presence of the Pd catalyst I (L = ligand II), reaction of PhOSO2Cl with 4-methoxyphenylboronic acid, followed by reaction with morpholine, gave 95% sulfonamide III.

Journal of the American Chemical Society published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Formula: C28H41N2P.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

 

Yang, Yang’s team published research in Organic Letters in 16 | CAS: 1160556-64-8

Organic Letters published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C22H23ClN4, Synthetic Route of 1160556-64-8.

Yang, Yang published the artcileHighly Selective Palladium-Catalyzed Cross-Coupling of Secondary Alkylzinc Reagents with Heteroaryl Halides, Synthetic Route of 1160556-64-8, the publication is Organic Letters (2014), 16(17), 4638-4641, database is CAplus and MEDLINE.

The highly selective palladium-catalyzed Negishi coupling of secondary alkylzinc reagents with heteroaryl halides is described [e.g., using a palladacycle precatalyst ligated by CPhos, 3-chlorobenzisothiazole was coupled with i-PrZnBr.LiCl to afford 3-isopropylbenzisothiazole in 78% yield (normal:rearranged ratio = 98:2)]. The development of a series of biarylphosphine ligands has led to the identification of an improved catalyst for the coupling of electron-deficient heterocyclic substrates. Preparation and characterization of oxidative addition complex (L)(Ar)PdBr provided insight into the unique reactivity of catalysts based on CPhos-type ligands in facilitating challenging reductive elimination processes.

Organic Letters published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C22H23ClN4, Synthetic Route of 1160556-64-8.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

 

Yang, Yang’s team published research in Angewandte Chemie, International Edition in 52 | CAS: 1160556-64-8

Angewandte Chemie, International Edition published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C18H20N2O12, Computed Properties of 1160556-64-8.

Yang, Yang published the artcilePalladium-Catalyzed Completely Linear-Selective Negishi Cross-Coupling of Allylzinc Halides with Aryl and Vinyl Electrophiles, Computed Properties of 1160556-64-8, the publication is Angewandte Chemie, International Edition (2013), 52(52), 14098-14102, database is CAplus and MEDLINE.

A linear-selective Negishi coupling reaction was developed and the synthesis of the target compounds was achieved by a reaction of (allyl)zinc reagents [i.e., (prenyl)zinc bromide, (farnesyl)zinc, etc.] with aryl halides, heteroaryl halides, vinyl halides. The reaction features mild reaction conditions and a broad reactant scope with respect to aryl halides and vinyl halides and (allyl)zinc coupling components. Under optimized reaction conditions [2′-(amino-κN)[1,1′-biphenyl]-2-yl-κC][2′-(dicyclohexylphosphino-κP)-N2,N2,N6,N6-tetramethyl[1,1′-biphenyl]-2,6-diamine](methanesulfonate-κO)palladium was used as a catalyst. This synthetic approach was applied to the preparation of 6-methyl-3-(3-methyl-2-buten-1-yl)-9H-carbazol-2-ol (siamenol).

Angewandte Chemie, International Edition published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C18H20N2O12, Computed Properties of 1160556-64-8.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

 

Babij, Nicholas R.’s team published research in Organic Letters in 16 | CAS: 1160556-64-8

Organic Letters published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Safety of 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine.

Babij, Nicholas R. published the artcileStereocontrolled Synthesis of Bicyclic Sulfamides via Pd-Catalyzed Alkene Carboamination Reactions. Control of 1,3-Asymmetric Induction by Manipulating Mechanistic Pathways, Safety of 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, the publication is Organic Letters (2014), 16(12), 3412-3415, database is CAplus and MEDLINE.

Arylmethyl and allylic cyclic sulfamides such as pyrroloisothiadiazinediones and pyridoisothiadiazinedione I [R = H, H2C:CHCH2; R1 = Ph, 4-t-BuC6H4, 4-MeOC6H4, 4-PhCOC6H4, 2-MeC6H4, 1-cyclohexenyl, Me(CH2)7CH:CH; X = CH2, CH2CH2; PMP = 4-MeOC6H4] were prepared in 43-89% yields and in 5:1-13:1 diastereoselectivities by intramol. alkene carboamination reactions of allyl-substituted heteroaryl sulfamides such as II (R = H, H2C:CHCH2; X = CH2, CH2CH2) with aryl triflates R1OTf [R1 = Ph, 4-t-BuC6H4, 4-MeOC6H4, 4-PhCOC6H4, 2-MeC6H4, 1-cyclohexenyl, Me(CH2)7CH:CH] in the presence of Pd(OAc)2 and the phosphine ligand CPhos III (Cy = cyclohexyl) in tert-butanol. The ligands of and conditions for palladium-catalyzed carboamination reactions may be tuned to favor either anti- and syn-aminopalladation reactions and thus to obtain different product diastereomers.

Organic Letters published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Safety of 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

 

Kirsch, Janelle K.’s team published research in Journal of Organic Chemistry in 83 | CAS: 1160556-64-8

Journal of Organic Chemistry published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Related Products of quinuclidine.

Kirsch, Janelle K. published the artcilePd-Catalyzed Alkene Carboheteroarylation Reactions for the Synthesis of 3-Cyclopentylindole Derivatives, Related Products of quinuclidine, the publication is Journal of Organic Chemistry (2018), 83(21), 13568-13573, database is CAplus and MEDLINE.

The Pd-catalyzed alkene carboheteroarylation of aryl and alkenyl triflate electrophiles bearing pendant alkenes with heteroaromatic nucleophiles affords substituted carbocycles with 3-indolyl or 3-pyrrolyl groups. The products are obtained in moderate to good yields, and the use of alkenyl triflate substrates produces products with high diastereoselectivities. The transformation is believed to proceed via a Friedel-Crafts-like reaction between the heteroaromatic nucleophile and an intermediate electrophilic palladium complex.

Journal of Organic Chemistry published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Related Products of quinuclidine.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

 

Peterson, Luke J.’s team published research in Organic Letters in 19 | CAS: 1160556-64-8

Organic Letters published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Recommanded Product: 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine.

Peterson, Luke J. published the artcileSynthesis of Cyclic Guanidines Bearing N-Arylsulfonyl and N-Cyano Protecting Groups via Pd-Catalyzed Alkene Carboamination Reactions, Recommanded Product: 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, the publication is Organic Letters (2017), 19(11), 2817-2820, database is CAplus and MEDLINE.

Palladium-catalyzed carboamination reactions of N-allylguanidines bearing cleavable N-cyano or N-arylsulfonyl protecting groups are described. The reactions afford cyclic guanidine products, e.g. I [Q = CN, Ts], in good yield, and transformations of substrates bearing internal alkenes proceed with high diastereoselectivity. Deuterium labeling studies indicate these transformations proceed via anti-aminopalladation pathways.

Organic Letters published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Recommanded Product: 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

 

Armstrong, Megan K.’s team published research in Journal of the American Chemical Society in 141 | CAS: 1160556-64-8

Journal of the American Chemical Society published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Related Products of quinuclidine.

Armstrong, Megan K. published the artcileDifferential Dihydrofunctionalization of Terminal Alkynes: Synthesis of Benzylic Alkyl Boronates through Reductive Three-Component Coupling, Related Products of quinuclidine, the publication is Journal of the American Chemical Society (2019), 141(15), 6173-6179, database is CAplus and MEDLINE.

The differential dihydrofunctionalization of terminal alkynes is accomplished through the reductive three-component coupling of terminal alkynes, aryl halides, and pinacolborane. The transformation results in hydrofunctionalization of both π-bonds of an alkyne in a single reaction promoted by cooperative action of a Cu/Pd catalyst system. The differential dihydrofunctionalization reaction has excellent substrate scope and can be accomplished in the presence of esters, nitriles, alkyl halides, epoxides, acetals, alkenes, aryl halides, and silyl ethers. Mechanistic experiments indicate that the reaction proceeds through Cu-catalyzed hydroboration followed by a 2nd hydrocupration. The resulting heterobimetallic complex is the key intermediate that participates in the subsequent Pd-catalyzed cross-coupling, which furnishes benzylic alkyl boronate products.

Journal of the American Chemical Society published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Related Products of quinuclidine.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

 

Stevens, Jason M.’s team published research in Organometallics in 41 | CAS: 1160556-64-8

Organometallics published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C8H15BrO2, Related Products of quinuclidine.

Stevens, Jason M. published the artcileAdvancing Base Metal Catalysis through Data Science: Insight and Predictive Models for Ni-Catalyzed Borylation through Supervised Machine Learning, Related Products of quinuclidine, the publication is Organometallics (2022), 41(14), 1847-1864, database is CAplus.

An expansive data set containing 33 substrates, 36 unique monophosphine ligands, and two solvents was produced for the NiCl2·6H2O catalyzed aryl (pseudo)halide borylation with tetrahydroxydiboron for a total of 1632 reactions. Exploratory data anal. revealed excellent reaction performance with simple triarylphosphines (P(p-F-Ph)3 and P(p-Anis)3) and mixed aryl-alkyl phosphines (PPh2Cy), in addition to the previously established high performance with Cy-JohnPhos. The data were used to train machine learning models that predicted out of sample reaction performance with a root-mean-square error of 18.4. The important features extracted from the models identified three phosphine parameters that offered reliable reactivity thresholds for identifying optimal ligand performance. The predictive models showed reasonable performance for predicting reaction yields employing ligands not included in model training, while the important feature boundaries accurately classified the performance of 10 of the 12 external ligands examined

Organometallics published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C8H15BrO2, Related Products of quinuclidine.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider