27486-17-5

Upstream product

• 106-39-8 bromochlorobenzene 
• 114701-85-8 (E)-(2-bromoethenyl)dibromoborane 
• 84109-17-1 2-methylphenylzinc chloride 
• 158871-10-4 2-methylbenzyl(diphenyl)phosphine oxide 
• 104-88-1 4-chlorobenzaldehyde 
• 1073-67-2 4-vinylbenzyl chloride 
• 6779-11-9 (2-methylphenyl)phosphonic acid 
• 52457-01-9 3-Methylcyclohexa-1,4-diene-3-carboxylic acid 
• 95-46-5 2-methylphenyl bromide 
• 932-31-0 ortho-tolylmagnesium bromide 
• 18684-97-4 (E)-1-(2-chlorovinyl)-4-chlorobenzene 
• 159386-40-0 1-[Chloro-(diphenyl-phosphinoyl)-methyl]-2-methyl-benzene 
• 529-20-4 2-methylphenyl aldehyde 
• 15286-11-0 diethyl o-tolylphosphonate 

Downstream Products

• 41064-50-0 (4-chlorophenyl)(2-methylphenyl)methanone 
• 1575599-21-1 C₁₅H₁₁ClO₂ 

Relevant academic research and scientific papers

N-Methylphenothiazine S-Oxide Enabled Oxidative C(sp2)–C(sp2) Coupling of Boronic Acids with Organolithiums via Phenothiaziniums

Herein, we report the development of a transition-metal-free oxidative C(sp2)–C(sp2) coupling of readily available boronic acids and organolithiums via phenothiazinium ions. Various biaryl, styrene, and diene derivatives were obtained using this reaction system. The key to this process is N-methylphenothiazine S-oxide (PTZSO), which allows efficient conversion of boronic acids to phenothiazinium ions. The mechanism of phenothiazinium formation using PTZSO was investigated using theoretical calculations and experiments, which provided insight into the unique reactivity of PTZSO.

Synthesis of Highly Substituted Arenes via Cyclohexadiene-Alkene C-H Cross Coupling and Aromatization

The development of a cross-coupling method for the regioselective β-alkenylation of 2,5-cyclohexadiene carboxylic acid derivatives to form ortho-alkenylarenes through in situ decarboxylation and aromatization is described. The carboxylic acid functionality is used as a traceless directing group for efficient and mild β-alkenylation. The modular sequence comprises a reductive Birch α-alkylation, ionic ?-alkylation followed by a Pd-catalyzed decarboxylative β-alkenylation with subsequent aromatization resulting in an overall three-fold ipso-para-ortho functionalization of readily accessed benzoic acid derivatives. Efficient synthesis of various alkyl-alkenylarenes under mild conditions in moderate to excellent yields is presented.

Room-temperature Kumada cross-coupling of unactivated aryl chlorides catalyzed by N-heterocylic carbene-based nickel(II) complexes

(Chemical Equation Presented) The Kumada cross-coupling reaction of a variety of unactivated aryl chlorides, vinyl chlorides, and heteroaryl chlorides catalyzed by nickel(II) complexes containing pyridine-functionalized NHC ligands is described. The catalysts are so active that the reactions proceed at room temperature in excellent yields.

Oxidative heck-type reaction involving cleavage of a carbon-phosphorus bond of arylphosphonic acids

Cleavage of a carbon-phosphorus bond is achieved under palladium catalysis in an oxidative Heck-type reaction which exploits arylphosphonic acids. The reaction of arylphosphonic acids with alkenes provides arylation products in good yields in the presence of TBAF with trimethylamine oxide as an oxidant. Copyright

Efficient synthesis of benzylphosphine oxides and E-stilbenes

A series of substituted benzylphosphine oxides has been synthesized by reduction of the corresponding (α-chlorobenzyl)phosphine oxide, derived from the benzaldehyde and chlorodiphenylphosphine, with either sodium borohydride (DMSO, 60-70 °C, 12 h) or tributyltin hydride and AIBN (C6H6, 80 °C, 2 h). Reaction of the (α-lithiobenzyl)phosphine oxide with aldehydes gave exclusively E-alkenes.

(E)-(2-Bromoethenyl)dibromoborane. A New Precursor for (E)-1,2-Disubstituted Ethenes

(E)-(2-Bromoethenyl)dibromoborane, prepared readily by the bromoboration of acetylene with tribromoborane, can be used as an effective precursor for the stereoselective synthesis of (E)-1,2-disubstituted ethenes.