58898-16-1

Upstream product

• 558-13-4 carbon tetrabromide 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 56506-90-2 (dibromomethyl)(triphenyl)phosphonium bromide 
• 75-25-2 Bromoform 
• 3167-63-3 diethyl chloromethylphosphonate 

Downstream Products

• 156780-40-4 (Z)-β-bromo-4-(N,N-dimethylamino)styrene 
• 66737-05-1 3-(4-(dimethylamino)phenyl)-1-phenylprop-2-yn-1-one 
• 35283-06-8 3-(4-(dimethylamino)phenyl)propiolic acid 
• 85608-98-6 (E)-β-bromo-4-(N,N-dimethylamino)styrene 
• 85608-98-6 C₁₀H₁₂BrN 
• 33429-13-9 benzo[d]thiazol-2-yl(4-(dimethylamino)phenyl)methanone 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 62167-09-3 4-((4-methoxyphenyl)ethynyl)-N,N-dimethylbenzenamine 

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.

Silver-catalyzed Double Decarboxylative Radical Alkynylation/Annulation of Arylpropiolic Acids with α-keto Acids: Access to Ynones and Flavones under Mild Conditions

Ynones are privileged building blocks in various organic syntheses of heterocyclic derivatives due to their multifunctional nature, and flavones are an important class of natural products with a wide range of biological activities. We describe the catalytic double decarboxylative alkynylation of arylpropiolic acids with α-keto acids. With Ag(I)/persulfate as the catalysis system, the valuable ynones bearing various substituents could be easily obtained. The introduction of hydroxyl substituent on ortho-site of α-keto acids make this strategy further applicable to the construction of flavone derivatives via heteroannulation in moderate to good yields with a similar silver-catalyzed system. The reactions proceed under relatively mild reaction conditions and tolerate a wide variety of functional groups. Control experiments indicated that both the reactions undergo radical processes. (Figure presented.).

Microwave-Assisted Dibromoolefination of Aromatic and Heteroaromatic Aldehydes and Ketones

Microwave (MW) irradiation was successfully employed to convert aromatic and heteroaromatic aldehydes and ketones efficiently to the corresponding dibromoolefins. Exemplified by the successful dibromoolefination of traditionally inert pyridyl-flanked carbonyls, MW activation significantly broadens the scope of this valuable transformation, although some limitations especially with electron-rich aromatic ketone derivatives remain.

CHBr3/TiCl4/Mg as an unusual nucleophilic CBr 2 carbenoid: Effective and chemoselective dibromomethylenation of aldehydes and ketones

We report that instead of using CBr4, CHBr3 can serve as a highly nucleophilic dibromomethylene carbenoid in chemoselective carbonyl dibromomethylenation. Successful application of the dibromomethylenation to various carbonyl compoun

Pd-catalyzed domino synthesis of internal alkynes using triarylbismuths as multicoupling organometallic nucleophiles

Figure presented The domino coupling reaction of 1,1-dibromo-1-alkenes with triarylbismuth nucleophiles has been demonstrated to furnish disubstituted alkynes directly under catalytic palladium conditions. The couplings of triarylbismuths as multicoupling nucleophiles with 3 equiv of 1,1-dibromo-1-alkenes are very fast, affording high yields of alkynes in a short reaction time. Thus, an efficient domino process has been accomplished using 1,1-dibromo-1-alkenes as surrogates for internal alkyne synthesis in couplings with triarylbismuths in a one-pot operation.

A one-pot procedure for the synthesis of alkynes and bromoalkynes from aldehydes

Alkynes R-C≡CH were obtained in good yield through a one-pot procedure by a sequence of reactions starting from a Wittig-type condensation of the aldehydes RCHO with the ylide derived from dibromomethyltriphenylphosphonium bromide 5. The same reactions could also be used to prepare the intermediate dibromoalkenes RCH=CBr2, and in certain cases, the bromoalkynes R-C≡CBr.

3α-Hydroxy-3β-(phenylethynyl)-5β-pregnan-20-ones: Synthesis and pharmacological activity of neuroactive steroids with high affinity for GABA(A) receptors

Neuroactive steroids that allosterically modulate GABA(A) receptors have potential uses as anticonvulsants, anxiolytics, and sedative-hypnotic agents. Recently, a series of pregnanes substituted with simple alkyl groups at the 3β-position were synthesized