84297-13-2

Upstream product

• 4361-83-5 α-benzylcinnamic acid 
• 18269-31-3 Methyl α-(trimethylsilyl)acrylate 
• 108-94-1 cyclohexanone 
• 591-51-5 phenyllithium 
• 100-52-7 benzaldehyde 
• 123-73-9 trans-Crotonaldehyde 
• 80-62-6 methacrylic acid methyl ester 
• 98-80-6 phenylboronic acid 
• 18020-59-2 methyl 3-hydroxy-2-methylidene-3-phenylpropionate 
• 71-43-2 benzene 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 67-64-1 acetone 

Relevant academic research and scientific papers

Mechanochemical Oxidative Heck Coupling of Activated and Unactivated Alkenes: A Chemo-, Regio- and Stereo-Controlled Synthesis of Alkenylbenzenes

In this work, we present an efficient mechanochemical strategy for chemo-, regio- and stereo-selective oxidative Heck coupling of readily accessible arylboron reagents/heteroaromatics with cyclic and acyclic olefins. Mono- and bis-arylation were achieved without the need of ligands, directing groups or prefunctionalized alkenes, and the reaction chemo-selectivity could be controlled by tuning of the oxidative system. This protocol offers the synthesis of alkenylbenzenes in broad substrate scope, satisfactory yields and excellent selectivity even in the gram scale. (Figure presented.).

Stereoselective homogeneous catalytic arylation of methyl methacrylate: Experimental and computational study

Catalytic systems trans-[PdCl2(DEA)2]/DEA and trans-[PdCl2(DEA)2]/[DEA][HAc], used in the model reaction of methyl methacrylate with iodobenzene, 4-iodoanisole, and bromobenzene, provide homogeneous catalysis, good regioselectivity and excellent stereoselectivity. The major product of the regioselective reaction is internal olefin. In all examined cases the only stereoisomer of the internal olefin methyl 3-phenyl-2-methylpropenoate is the E-isomer, whereas the only stereoisomer of the double arylated reaction product methyl 2-benzyl-3- phenylpropenoate is the Z-isomer. A DFT study, which investigates mechanistic aspects of migratory insertion, β-hydride elimination and reductive elimination of this phosphine-free Heck reaction, is in agreement with our experimental findings.

Rhodium fluorapatite catalyst for the synthesis of trisubstituted olefins via cross coupling of Baylis-Hillman adducts and arylboronic acids

(Chemical Equation Presented) Treatment of fluorapatite (prepared by incorporating basic species F- in apatite in situ by coprecipitation) with an aqueous solution of RhCl3 resulted in rhodium-exchanged fluorapatite catalyst (RhFAP),

Access to stereodefined trisubstituted alkenes via rhodium-catalyzed 1,4-addition of potassium trifluoro(organo)borates to Baylis-Hillman adducts

In the presence of a rhodium catalyst, unactivated Baylis-Hillman adducts reacted regioselectively with potassium trifluoro(organo)borates to afford stereodefined trisubstituted alkenes with good yields. This highly efficient reaction (aerobic conditions,

The Friedel-Crafts reaction of the Baylis-Hillman adducts

A simple and convenient methodology for the stereoselective construction of 2-benzyl substituted trisubstituted olefins via sulfuric acid catalyzed Friedel-Crafts reaction of benzene with Baylis-Hillman adducts is described.

Palladium-catalyzed cross-coupling of aryl and alkenyl boronic acids with alkenes via oxidative addition of a carbon-boron bond to palladium(0)

Arylboronic acids react with alkenes in acetic acid at 25 deg C in the presence of a catalytic amount of palladium(II) acetate together with sodium acetate to give the corresponding aryl-substituted alkenes in high yields.Alkenylboronic acids react with alkenes under similar conditions to give the corresponding conjugated dienes stereospecifically, but the product yields are lower, compared with those from arylboronic acids.Similar treatment of sodium tetraphenylborate (NaBPh4) with alkenes also affords the corresponding phenylated alkenes in high yields together with biphenyl and benzene as side products.Oxidative addition of a carbon-boron bond to palladium(0), formed in situ, to give an organopalladium(II) species is assumed to be the key step of these cross-coupling reactions. Key words: Boronic acid; Aryl; Alkenyl; Alkene; Palladium; Oxidative addition

Michael addition of methyl 2-(trimethysily)propenoate with organomagnesiums or organolithiums leading to 1:1 and / or 2:1 adducts and subsequent peterson olefination by condensation with carbonyl compounds

Michael addition of methyl 2-(trimethylsilyl)propenoate with organomagnesiums or organolithiums leads to 1:1 and/or 1:2 adduct anions which can be utilized in the subsequent step of Peterson olefination with carbonyl compounds. The 1:1/1:2 ratio depends u

MICHAEL ADDITION-PETERSON OLEFINATION SEQUENCE OF METHYL 2-(TRIMETHYLSILYL)ACRYLATE AS A CONVENIENT METHOD FOR CONSECUTIVE FORMATION OF CARBON-CARBON SINGLE AND DOUBLE BONDS

A convenient method for the consecutive formation of carbon-carbon single and double bonds is presented with the example of the Peterson olefination of the carbanions resulted from the Michael addition of organometallics to methyl 2-(trimethylsilyl)acryla