Category: 928836-00-4

Chen, Chaohuang published the artcilePalladium(II)-Catalyzed Aminotrifluoromethoxylation of Alkenes: Mechanistic Insight into the Effect of N-Protecting Groups, Application of 2,2-Diallylpent-4-en-1-amine, the publication is Chinese Journal of Chemistry (2020), 38(4), 346-350, database is CAplus.

An efficient palladium-catalyzed regioselective 5-exo aminotrifluoromethoxylation of alkenes was established herein, which provided a practical route toward the synthesis of OCF₃-containing pyrrolidines such as I [R¹ = H, allyl, 4-ClC₆H₄, etc.; R² = allyl, Bn, 4-FC₆H₄, etc.; R¹R² = (CH₂)₃, (CH₂)₄, (CH₂)₂O(CH₂)₂, etc.] and II. Tert-Butyloxycarbonyl (Boc) as an amino protecting group played a significant role in both chemo- and regioselectivities. In addition, preliminary mechanistic studies revealed that amino protecting group of substrates and counter anion of palladium catalyst play critical roles in reaction efficiency presumably due to an isomerization of alkyl- Pd(II) intermediates. Moreover, the asym. 5-exo aminotrifluoromethoxylation reaction had also been achieved by introducing a sterically bulky pyridinyl-oxazoline ligand.

Chinese Journal of Chemistry published new progress about 928836-00-4. 928836-00-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain, name is 2,2-Diallylpent-4-en-1-amine, and the molecular formula is C11H19N, Application of 2,2-Diallylpent-4-en-1-amine.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Manna, Kuntal published the artcileHighly enantioselective zirconium-catalyzed cyclization of aminoalkenes, Name: 2,2-Diallylpent-4-en-1-amine, the publication is Journal of the American Chemical Society (2013), 135(19), 7235-7250, database is CAplus and MEDLINE.

Group 4 half-sandwich cyclopentadienyl complexes with pendant chiral oxazoline ligands were prepared and examined as catalysts for enantioselective intramol. hydroamination of alkenamines, yielding chiral 5-7-membered saturated nitrogen heterocycles. Aminoalkenes are catalytically cyclized in the presence of cyclopentadienylbis(oxazolinyl)borato group 4 complexes {PhB(¦Ç⁵-C₅H₄)(Ox^R)₂}M(NMe₂)₂ (M = Ti, Zr, Hf; Ox^R = 4,4-dimethyl-2-oxazoline, 4S-isopropyl-5,5-dimethyl-2-oxazoline, 4S-tert-butyl-2-oxazoline) at room temperature and below, affording five-, six-, and seven-membered N-heterocyclic amines with enantiomeric excesses of >90% in many cases and up to 99%. Mechanistic investigations of this highly selective system employed synthetic tests, kinetics, and stereochem. Secondary aminopentene cyclizations require a primary amine (1-2 equiv vs. catalyst). Aminoalkenes are unchanged in the presence of a zirconium monoamido complex {PhB(C₅H₄)(Ox^4S-iPr,Me₂)₂}Zr(NMe₂)Cl or a cyclopentadienylmono(oxazolinyl)borato zirconium diamide {Ph₂B(C₅H₄)(Ox^4S-iPr,Me₂)}Zr(NMe₂)₂. Plots of initial rate vs. [substrate] show a rate dependence that evolves from first-order at low concentration to zero-order at high concentration, and this is consistent with a reversible substrate-catalyst interaction preceding an irreversible step. Primary kinetic isotope effects from substrate conversion measurements (k’_obs^(H)/k’_obs^(D) = 3.3 ¡À 0.3) and from initial rate anal. (k₂^(H)/k₂^(D) = 2.3 ¡À 0.4) indicate that a N-H bond is broken in the turnover-limiting and irreversible step of the catalytic cycle. Asym. hydroamination/cyclization of N-deutero-aminoalkenes provides products with higher optical purities than obtained with N-protio-aminoalkenes. Transition state theory, applied to the rate constant k₂ that characterizes the irreversible step, provides activation parameters consistent with a highly organized transition state (¦¤S? = -43(7) cal¡¤mol^-1 K^-1) and a remarkably low enthalpic barrier (¦¤H? = 6.7(2) kcal¡¤mol^-1). A six-centered, concerted transition state for C-N and C-H bond formation and N-H bond cleavage involving two amidoalkene ligands is proposed as most consistent with the current data.

Journal of the American Chemical Society published new progress about 928836-00-4. 928836-00-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain, name is 2,2-Diallylpent-4-en-1-amine, and the molecular formula is C11H19N, Name: 2,2-Diallylpent-4-en-1-amine.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Liu, Gong-Qing published the artcileRegioselective copper(II)-mediated bromoamination of unfunctionalized olefins: An efficient route to N-heterocyclic compounds, Application In Synthesis of 928836-00-4, the publication is Advanced Synthesis & Catalysis (2014), 356(10), 2303-2310, database is CAplus.

Bromoamination of non-functionalized olefins was realized under mild conditions using CuBr₂ as both reaction promoter and Br source. The reactions could be carried out under open air at ambient temperature, and both N-alkylated and N-tosylated substrates could be converted to the corresponding N-heterocyclic compounds in high regioselectivity and good isolated yields. A variety of biol. important structures could be obtained via subsequent nucleophilic substitution reactions.

Advanced Synthesis & Catalysis published new progress about 928836-00-4. 928836-00-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain, name is 2,2-Diallylpent-4-en-1-amine, and the molecular formula is C11H19N, Application In Synthesis of 928836-00-4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Huynh, Khoi published the artcileEnantioselective hydroamination/cyclization of aminoalkenes by (bis)-C₂ symmetric and (mono)-C₂ symmetric anionic tetraamide complexes of La(III), Related Products of catalysis-chemistry, the publication is Tetrahedron Letters (2015), 56(23), 3658-3661, database is CAplus.

Enantioselective hydroamination/cyclizations of several monosubstituted and disubstituted aminoalkenes were achieved, catalyzed by tetracoordinate anionic lanthanum(III) complexes with chiral (R)-N,N’-bis(dibenzosuberan-5-yl)-1,1′-binaphthalene-2,2′-diamine. Yttrium(III) complexes were also prepared, but the La(III) complexes showed higher activity and enantioselectivity.

Tetrahedron Letters published new progress about 928836-00-4. 928836-00-4 belongs to catalysis-chemistry, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain, name is 2,2-Diallylpent-4-en-1-amine, and the molecular formula is C11H19N, Related Products of catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia