67590-77-6

Upstream product

• 592-41-6 1-hexene 
• 62-38-4 phenylmercuric acetate 
• 13633-27-7 1-(hexa-1,2-dienyl)benzene 
• 182740-29-0 (Z)-Dodec-3-en-1,5-diin 
• 140-88-5 ethyl acrylate 
• 2497-18-9 2-hexenyl acetate 
• 17869-38-4 3-trimethylsiloxy-1-hexene 
• 100-58-3 phenylmagnesium bromide 
• 120989-99-3 [(2E)-hex-2-en-1-yloxy]benzene 
• 110-62-3 pentanal 
• 591-50-4 iodobenzene 
• 2497-18-9 (E)-2-hexen-1-yl acetate 
• 627-19-0 1-Pentyne 
• 300-57-2 allylbenzene 

Downstream Products

• 1370038-00-8 butyl (E)-3-(2-((Z)-hex-2-enyl)phenyl)acrylate 
• 1370037-99-2 butyl (E)-3-(2-((E)-hex-2-enyl)phenyl)acrylate 

Relevant academic research and scientific papers

Aziridine Opening via a Phenonium Ion Enables Synthesis of Complex Phenethylamine Derivatives

We report that the treatment of unsymmetrical 2,3-disubstituted aziridines with TiCl4 yields β-phenethylamine products via the intermediacy of a phenonium ion. Derivatization of the products obtained via this method is demonstrated. Computational analysis of the reaction pathway provides insight into the reaction mechanism, including the selectivity of the phenonium opening.

Cationic Tungsten Imido Alkylidene N-Heterocyclic Carbene Complexes That Contain Bulky Ligands

Neutral and cationic tungsten imido alkylidene complexes of the general formulas W(NtBu)(CHR1)(OR2)Cl(NHC), W(N-2,6-bis(2,4,6-tri-iPr-C6H4)phenyl)(CHR1)Cl2(NHC), [W(NtBu)(CHR1)(OR2)(NHC)][B(ArF)4] and [W(N-2,6-bis(2,4,6-tri-iPr-C6H4)phenyl)(CHR1)Cl(NHC)][B(ArF)4] (R1= CMe3, CMe2Ph; R2= sterically demanding alkoxide; B(ArF)4= tetrakis(3,5-(CF3)2-C6H3)borate; NHC = N-heterocyclic carbene) were prepared. Two electronically different NHCs, namely 1,3-dimethylimidazol-2-ylidene (IMe) and 1,3-dimethyl-4,5-dichloroimidazol-2-ylidene (IMeCl), as well as a variety of terphenolates and a chiral biphenolate were employed.Z-selective homometathesis (HM) of unfunctionalized olefins was achieved with a selectivity of up to 90% and decent turnover numbers (TON) of up to 480 in the HM of 1-dodecene. Additionally, the reactivity of the cationic tungstentert-butylimido complexes in the reaction with vinyltrimethylsilane and ethylene was investigated, which yielded the corresponding silyl-alkylidene complex and, for the first time, a fully characterized cationic tungsten(IV) NHC ethylene complex.

P/N Heteroleptic Cu(I)-Photosensitizer-Catalyzed Deoxygenative Radical Alkylation of Aromatic Alkynes with Alkyl Aldehydes Using Dipropylamine as a Traceless Linker Agent

A deoxygenative radical alkylation of aromatic alkynes with alkyl aldehydes for the preparation of allylarenes has been successfully achieved. This transformation is accomplished through the reaction of alkyl aldehydes with alkynes in the presence of dipr

A Fluorescence-Based High-Throughput Screening Method for Olefin Metathesis Using a Ratiometric Fluorescent Probe

(Z)-1,8-Di(pyren-1-yl)oct-4-ene (1) was prepared as a probe for olefin metathesis. The conversions of substrate by olefin metathesis under various conditions were calculated using the ratiometric fluorescence intensity change of 1. The conversions calcula

Method for synthesizing 1,2-dissubstituted olefin compounds by alkyne alkylation

The invention discloses a method for synthesizing 1,2-dissubstituted olefin compounds by high-selectivity alkyne alkylation. The method comprises the following specific steps: a photosensitizer, an alkyne compound represented as the formula I and hantzsch

Controllable, Sequential, and Stereoselective C-H Allylic Alkylation of Alkenes

The direct conversion of C-H bonds into new C-C bonds represents a powerful approach to generate complex molecules from simple starting materials. However, a general and controllable method for the sequential conversion of a methyl group into a fully substituted carbon center remains a challenge. We report a new method for the selective and sequential replacement of three C-H bonds at the allylic position of propylene and other simple terminal alkenes with different carbon groups derived from Grignard reagents. A copper catalyst and electron-rich biaryl phosphine ligand facilitate the formation of allylic alkylation products in high branch selectivity. We also present conditions for the generation of enantioenriched allylic alkylation products in the presence of catalytic copper and a chiral phosphine ligand. With this approach, diverse and complex products with substituted carbon centers can be generated from simple and abundant feedstock chemicals.

OLEFIN METATHESIS CATALYSTS

This invention relates generally to metathesis catalysts and the use of such catalysts in the metathesis of olefins and olefin compounds, more particularly, in the use of such catalysts in Z and E selective olefin metathesis reactions. The invention has utility in the fields of organometallics and organic synthesis.

Reactivity of mixed organozinc and mixed organocopper reagents: 14. Phosphine-nickel catalyzed aryl-allyl coupling of (n-butyl)(aryl)zincs. Ligand and substrate control on the group selectivity and regioselectivity

The group selectivity and regioselectivity in the allylation of mixed (n-butyl)(aryl)zinc reagents in THF depends on the nickel catalyst type and also on nature of the allylic substrate. Allylation of (n-butyl)(phenyl)zinc reagent with alkyl substituted primary allylic chlorides and acetates in the presence of NiCl2(dppf) catalysis affords the phenyl coupling product with γ-selectivity. However, allylation with aryl substituted primary allylic substrates results in both phenyl- and alkyl-coupling products with medium α-selectivity in the presence of NiCl2(dppf) catalysis whereas phenyl coupling product is formed with α-selectivity in the presence of NiCl2(Ph3P)2 catalysis. This new NiCl2(dppf) catalyzed protocol for γ-selective aryl allylation of (n-butyl)(aryl)zinc reagents with alkyl substituted primary allylic chlorides in THF at room temperature provides an atom economic alternative to allylation of (aryl)2Zn reagents. A mechanism for the dependence of group selectivity and regioselectivity of Ni catalyzed allylation of (n-butyl)(aryl)zinc reagents on the catalyst ligand and the substrate was proposed.

A vesicular self-assembled amphiphilic palladium NNC-pincer complex-catalyzed allylic arylation of allyl acetates with sodium tetraarylborates in water

Abstract The allylic arylation of various allyl acetates with sodium tetraarylborates proceeded in water in the presence of a vesicular self-assembled amphiphilic palladium NNC-pincer complex to give the corresponding arylated products in high yield, wher

A palladium NNC-pincer complex: An efficient catalyst for allylic arylation at parts per billion levels

Allylic arylation of allylic acetates by sodium tetraarylborates in the presence of ppb to ppm (molar) loadings of a palladium NNC-pincer complex catalyst in methanol at 50°C gave the corresponding arylated products in excellent yields. Total turnover numbers of up to 500 000 000 and turnover frequencies of up to 11 250 000 h-1 were achieved.