27911-12-2

Upstream product

• 925-90-6 ethylmagnesium bromide 
• 4392-24-9 Cinnamyl bromide 
• 3909-83-9 (+/-)-4-chloro-1-phenyl-pent-2ξ-ene 
• 91076-08-3 bis(dimethylphenylsilyl)zinc 
• 148614-78-2 (E)-1-phenyl-1-penten-3-yl phenyl carbamate 
• 135758-87-1 (1S,2E)-benzoic acid 1-methyl-3-phenylallyl ester 
• 917-64-6 methyl magnesium iodide 
• 768-56-9 4-Phenylbut-1-ene 
• 109-67-1 1-penten 
• 71-43-2 benzene 
• 4250-81-1 1-phenyl-1-pentyne 
• 20599-27-3 1-bromopent-2-ene 
• 100-58-3 phenylmagnesium bromide 
• 60-29-7 diethyl ether 

Downstream Products

• 122-78-1 phenylacetaldehyde 
• 3508-98-3 1-Cyano-1-phenylpentan 

Relevant academic research and scientific papers

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.

CATALYSTS AND METHODS FOR FORMING ALKENYL AND ALKYL SUBSTITUTED ARENES

Embodiments of the present disclosure provide for Rh(I) catalysts, methods of making alkenyl substituted arenes (e.g., allyl arene, vinyl arene, and the like), methods of making alkyl substituted arenes, and the like.

Catalytic Semireduction of Internal Alkynes with All-Metal Aromatic Complexes

A simple catalytic method involving all-metal aromatic frameworks as precatalysts ensures an efficient route to (Z)-alkenes. Aromatic triangular palladium clusters were used to reduce internal alkynes without any trace of the formation of alkane side products. These trinuclear complexes provide a catalytic system that parallels the activity and selectivity of their best mononuclear peers, and the catalyst likely operates through complementary mechanisms.

Copper-catalyzed asymmetric allylic substitution with aryl and ethyl Grignard reagents

Phenyl- and ethyl-magnesium bromides undergo regioselective asymmetric allylic substitution with high enantioselectivity under the catalysis of chiral amidophosphane-copper(i) complexes. The Royal Society of Chemistry.

Mechanistic insight into copper-catalysed allylic substitutions with bis(triorganosilyl) zincs. Enantiospecific preparation of α-chiral silanes

Isotopic desymmetrisation, as well as (stereo)chemical correlation, has illuminated significant aspects of the σ-π-σ mechanism of copper-catalysed allylic substitution reactions: an enantiospecific and regioselective access to α-chiral silanes is presente

REACTION OF 1,3-ALKADIENES WITH ARENEDIAZONIUM CHLORIDES IN THE PRESENCE OF IRON(II) CHLORIDE

The reaction of arenediazonium chlorides with 1,3-alkadienes in the presence of iron(II) chloride was investigated.It was established that the reaction takes place with the formation of products from chloroarylation of the dienes, telomerization, and additive dimerization.A method is proposed for the synthesis of diaryloctatetraenes containing substituents in the aromatic rings and in the aliphatic chain.