104151-26-0

Upstream product

• 110-82-7 cyclohexane 
• 3179-10-0 (E)-1-methoxy-4-(2-nitrovinyl)benzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 695-12-5 vinylcyclohexane 
• 81602-60-0 1,2-dibromo-1-cyclohexylethane 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1093686-52-2 1-cyclohexylvinyl tosylate 
• 93296-09-4 4-methoxyphenylzinc chloride 
• 623-12-1 4-chloromethoxybenzene 
• 57002-01-4 (E)-(2-cyclohexylvinyl)boronic acid 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 
• 1539-59-9 4-cyclohexyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester 
• 626-62-0 Cyclohexyl iodide 

Downstream Products

• 104151-27-1 1,2-dibromo-1-(3-bromo-4-methoxyphenyl)-cyclohexylethene 
• 141298-90-0 1-(1,2-Dichloro-2-cyclohexyl-ethyl)-4-methoxy-benzene 

Relevant academic research and scientific papers

Improved one-pot synthesis of styryl tetrahydrofurans and cyclohexanes by radical addition to β-nitrostyrenes in the presence of benzoyl peroxide

Stereoselective styryl derivatives have been prepared based on radical substitution (addition-elimination) of heterocycles or cyclohydrocarbons units to (E)-β-nitrostyrenes 1 using a common radical initiator benzoyl peroxide. High reactivity and selectivity with wide substrate scope were attained by using this easy methodology. The reactions using easily obtained and one-pot potential starting materials gave excellent trans-selectivity with medium to high yields in all cases. Synthetic utility of this approach has been demonstrated by the preparation of various trans-styryl derivatives.

Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinyl carboxylic acids via a radical process

A Fe(acac)3-catalyzed decarboxylative coupling of 2-(aryl)vinyl carboxylic acids with cycloalkanes was developed by using DTBP as an oxidant through a radical process. This reaction tolerates a wide range of substrates, and products are obtained in good to excellent yields (71-95%). The reaction also shows excellent stereoselectivity, and only trans-isomers are obtained.

Cobalt-catalyzed heck-type reaction of alkyl halides with styrenes

(Chemical Equqtion Presentation) A cobalt complex, CoCl2[1,6-bis(diphenylphosphino)hexane], catalyzes an alkylation reaction of styrenes in the presence of Me3SiCH2MgCl in ether to yield β-alkylstyrenes. A variety of alkyl halides including alkyl chlorides can be employed as an alkyl source. A radical mechanism is strongly suggested for this alkylation reaction. Copyright

Copper-catalyzed oxidative decarboxylative alkylation of cinnamic acids with 4-alkyl-1,4-dihydropyridines

We have developed a new oxidative decarboxylation of cinnamic acids with 4-alkyl-1,4-dihydropyridines to construct C(sp3)-C(sp2) bonds in the presence of copper catalyst and dicumyl peroxide (DCP). A variety of internal alkenes have been obtained with mild conditions, broad substrate scope and excellent functional group tolerance. This method has significant potential for application by using inexpensive and stable cinnamic acids instead of alkenyl halides and nitro-olefins. This journal is

Photocatalytic dual decarboxylative alkenylation mediated by triphenylphosphine and sodium iodide

An efficient photocatalytic dual decarboxylative alkenylation of α,β-unsaturated carboxylic acids and alkyl N-hydroxyphthalimide (NHP) esters mediated by triphenylphosphine and sodium iodide has been developed. This protocol proceeds under 456-nanometer irradiation by visible blue light in the absence of transition metals or organic dye based photoredox catalysts. The reaction is successfully applied to a wide range of redox-active esters derived from aliphatic carboxylic acids (1°, 2° and 3°) and α-amino acids, enabling transformations of diverse α,β-unsaturated carboxylic acids to α,β-alkylated styrenes with high efficiency and excellent selectivity under mild conditions.

Visible-Light-Promoted Cross-Coupling of N-Alkylpyridinium Salts and Nitrostyrenes

A stereoselective, denitrative cross-coupling of β-nitrostyrenes with N-alkylpyridinium salts for the preparation of functionalized styrenes has been developed. The visible-light-induced reaction proceeds without any catalyst at ambient temperature. Broad in scope and tolerant to multiple functional groups, the moderately yielding transformation is orthogonal to several traditional metal-catalyzed cross-couplings.

Copper porphyrin-catalyzed cross dehydrogenative coupling of alkanes with carboxylic acids: Esterification and decarboxylation dual pathway

A dual-functional copper porphyrin-catalyzed cross dehydrogenative coupling (CDC) of carboxylic acids with alkanes was reported firstly. The reaction gives allylic esters or alkylalkenes depending on the carboxylic acid substrates. Copper porphyrin catalyzed CDC method has the superiority of short reaction time, good functional group tolerance, base and solvent free, producing target products in an atom-economic manner.

Stereospecific Iron-Catalyzed Carbon (sp2)-Carbon (sp2) Cross-Coupling of Aryllithium with Vinyl Halides

We present herein an efficient synthetic protocol involving iron-catalyzed cross-coupling of organolithium compounds with vinyl halides as key coupling partners. More than 30 examples were obtained with moderate to good yields and high stereoselectivities. The practicality of this method is evidenced by a gram-scale synthesis. In addition, a preliminary mechanistic investigation was also performed.

Visible-Light-Mediated Alkenylation of Alkyl Boronic Acids without an External Lewis Base as an Activator

Herein we report a protocol for the direct visible-light-mediated alkenylation of alkyl boronic acids at room temperature without an external Lewis base as an activator, and we propose a mechanism involving benzenesulfinate activation of the alkyl boronic acids. The protocol permits the efficient functionalization of a broad range of cyclic and acyclic primary and secondary alkyl boronic acids with various alkenyl sulfones. We demonstrated its utility by preparing or functionalizing several pharmaceuticals and natural products.

Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins

The dealkenylative alkenylation of alkene C(sp3)?C(sp2) bonds has been an unexplored area for C?C bond formation. Herein 64 examples of β-alkylated styrene derivatives, synthesized through the reactions of readily accessible feedstock olefins with β-nitrostyrenes by ozone/FeII-mediated radical substitutions, are reported. These reactions proceed with good efficiencies and high stereoselectivities under mild reaction conditions and tolerate an array of functional groups. Also demonstrated is the applicability of the strategy through several synthetic transformations of the products, as well as the syntheses of the natural product iso-moracin and the drug (E)-metanicotine.