85608-98-6

Upstream product

• 58898-16-1 2,2-dibromo-1-<4'-(N,N-dimethylamino)phenyl>ethene 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 1552-96-1 4-dimethylaminocinnamic acid 

Downstream Products

• 1013937-36-4 C₁₆H₁₆⁽¹⁸⁾FN 
• 405-86-7 (E)-4-(4-fluorostyryl)-N,N-dimethylaniline 
• 85608-98-6 (E)-β-bromo-4-(N,N-dimethylamino)styrene 
• 1206103-18-5 (1E,3E)-1-[4-(dimethylamino)phenyl]-4-(4-hydroxy-3-methoxyphenyl)-1,3-butadiene 
• 17573-94-3 4-ethynyl-N,N-dimethylaniline 

Relevant academic research and scientific papers

Nickel-Catalyzed, Regio- and Enantioselective Benzylic Alkenylation of Olefins with Alkenyl Bromide

A NiH-catalyzed migratory hydroalkenylation reaction of olefins with alkenyl bromides has been developed, affording benzylic alkenylation products with high yields and excellent chemoselectivity. The mild conditions of the reaction preclude olefinic products from undergoing further isomerization or subsequent alkenylation. Catalytic enantioselective hydroalkenylation of styrenes was achieved by using a chiral bisoxazoline ligand.

Iron-Catalyzed Reductive Vinylation of Tertiary Alkyl Oxalates with Activated Vinyl Halides

We present herein a rare and efficient method for the creation of vinylated all carbon quaternary centers via Fe-catalyzed cross-electrophile coupling of vinyl halides with tertiary alkyl methyl oxalates. The reaction displays excellent functional group tolerance and broad substrate scope, which allows cascade radical cyclization and vinylation to afford complex bicyclic and spiral structural motifs. The reaction proceeds via tertiary alkyl radicals, and the putative vinyl-Br/Fe complexation appears to be crucial for activating the alkene and enabling a possibly concerted radical addition/C-Fe forming process.

Nucleophile-selective cross-coupling reactions with vinyl and alkynyl bromides on a dinucleophilic aromatic substrate

A nucleophile-selective cross-coupling reaction on an aromatic compound bearing two metal groups, Bpin and SnMe3, has been developed. Previously, only aryl bromides and iodides could be used as electrophilic components, but in this work, the scope could be extended to vinyl and alkynyl bromides as electrophiles. This means that the roles typical in Sonogashira couplings or Heck reactions of the aromatic ring as the dielectrophile coupling to vinyl and alkynyl metal species are reversed, which presents a new tool for organic synthesis. The first nucleophilic site to react is the stannyl group, and subsequently, a Suzuki-Miyaura cross-coupling reaction can take place on the same molecule.

Novel system for decarboxylative bromination of α,β-unsaturated carboxylic acids with diacetoxyiodobenzene

A simple and mild method for the conversion of varieties of α,β-unsaturated carboxylic acids to the corresponding bromoalkenes using diacetoxyiodobenzene (IBD) in combination with tetraethyl-ammonium bromide (TEAB) at room temperature is discussed. Advantages of this system are short reaction time, easy work up and gave good to excellent yields.