5751-28-0

Upstream product

• 116659-84-8 (Z)-3-(naphthalen-1-yl)acrylic acid 
• 108-88-3 toluene 
• 13026-12-5 (E)-3-(naphthalen-1-yl)acrylic acid 
• 98978-44-0 (E)-3-(1-naphthyl)prop-2-en-1-ol 
• 98-80-6 phenylboronic acid 
• 66-77-3 1-naphthaldehyde 
• 98978-43-9 ethyl 3-(naphthalen-1-yl)acrylate 
• 4735-49-3 1-[(E)-2-nitroethenyl]naphthalene 
• 1539-57-7 diethyl 2,6-dimethyl-4-benzyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 87100-28-5 pinacol benzylboronate 
• 300-57-2 allylbenzene 
• 91-20-3 naphthalene 
• 37630-26-5 β-(1-naphthyl)nitroethylene 
• 22871-77-8 5,5-dimethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborinane 

Relevant academic research and scientific papers

Palladium catalyzed reaction of α-chloromethylnaphthalene with olefins

The reaction of α-chloromethylnaphthalene with various olefins in the presence of palladium acetate produces three different kinds of products. The coupling products with the olefinic bond conjugated to the naphthalene ring are the major products for the

A photocatalyst-free photo-induced denitroalkylation of β-nitrostyrenes with 4-alkyl substituted Hantzsch esters at room temperature

A photocatalyst-free stereoselectively photo-induced strategy for the denitroalkylation of β-nitrostyrenes using 4-alkyl substituted Hantzsch esters as the alkyl source under xenon lamp irradiation is developed. The reaction proceeds at room temperature and affords the corresponding products in moderate to excellent yields. The oxidant di-t-butyl peroxide serves as an efficient radical initiator under irradiation of a Xenon lamp, initiating alkyl radicals from the 4-alkyl substituted Hantzsch esters.

Palladium-catalyzed reaction of γ-silylated allyl acetates proceeding through 1,2-shift of a substituent on silicon

The palladium-catalyzed reaction of γ-silylated allyl acetates with water in the presence of CsF induces a previously unprecedented 1,2-shift of a substituent on silicon to produce allylsilanes in situ. The catalytic activity of the palladium increased when using an electron-poor phosphine ligand possessing fluorinated substituents. Further investigation of the reaction revealed that the approximate order of the migratory aptitude of groups from silicon was PhC≡C, allyl > Bn > Ph, vinyl > alkyl (Me, Et). A density functional theory study was employed to explore the reaction mechanism. Finally, the Hosomi–Sakurai-type allylation of aldehydes with in situ-generated α,γ-disubstituted allylsilanes was also investigated.

Nickel-Catalyzed Direct Coupling of Allylic Alcohols with Organoboron Reagents

The direct coupling of allylic alcohols with arylboronic acids or their derivatives catalyzed by Ni(cod)2 in the presence of a catalytic amount of base has been developed. A wide variety of allylic substrates or arylboronic acids turned out to be applicable to this catalytic system. The present method does not require the use of ligands for stabilizing the nickel catalyst in most cases or additional activators for activation of allylic alcohols.

S,O-ligand-promoted palladium-catalyzed C–H olefination of arenes with allylic substrates

An efficient catalytic system for the C–H olefination of arenes with different allylic substrates is reported. The catalytic system is based on Pd(OAc)2 and a readily accessible bidentate S,O-ligand. The methodology shows high activity with a wide range of arenes, including bulky and, electron-rich and -poor arenes. The applicability of this catalyst is demonstrated in the late-stage functionalization of the complex molecule O-methylestrone.

Synthesis of (E)-prop-1-ene-1,3-diyldibenzene derivatives via direct decarboxylative coupling of α,β-unsaturated carboxylic acids with benzyl boronic acid pinacol ester

The first copper-catalyzed cross-coupling reaction between benzyl boronic acid pinacol ester and α,β-unsaturated carboxylic acids was described. The ready availability of the starting materials and excellent E selectivity make this protocol a safe and operationally convenient strategy for the efficient synthesis of (E)-prop-1-ene-1,3-diyldibenzene derivatives.

Copper-catalyzed oxidative alkenylation of C(sp3)-H bonds via benzyl or alkyl radical addition to β-nitrostyrenes

A new method for the preparation of (E)-β-alkylstyrene derivatives has been developed via the addition of a benzyl or alkyl radical to β-nitrostyrenes using di-tert-butyl peroxide (DTBP) as the oxidant in the presence of Cu powder catalyst. The C-H bonds in various toluene derivatives, ethers, alkanes and alcohols were successfully converted into C-C bonds to yield the corresponding (E)-β-alkylstyrene derivatives in moderate to good yields.

Alkyl transfer from C-C cleavage: Replacing the nitro group of nitro-olefins

Alkyl substituted Hantzsch esters are rationally used as alkylation reagents to replace the nitro groups of nitro olefins to give excellent yields of trans-olefins. The reaction mechanism is considered to proceed through a free radical mechanism, which is different from the corresponding transfer alkylation of imines. This journal is the Partner Organisations 2014.

Iron-catalyzed direct alkenylation of sp3(C-H) bonds via decarboxylation of cinnamic acids under ligand-free conditions

An example of highly efficient low-cost ferrocene-catalyzed decarboxylative C(sp2)-C(sp3) coupling reactions via C-H functionalization has been developed successfully. It is noteworthy that nanoparticles of Fe3O4 could be used as a reusable catalyst for 7 times in the absence of ligand.

Oxygen-promoted Pd(II) catalysis for the coupling of organoboron compounds and olefins

(Matrix presented) Reported herein is a mild and efficient Pd(ll) catalysis, leading to the formation of carbon-carbon bonds between a broad spectrum of organoboron compounds and alkenes. Molecular oxygen was employed to reoxidize the resultant Pd(0) species back to Pd(ll) during catalytic cycles. This oxygen protocol promoted the desired Pd(ll) catalysis, whereas it retarded competing Pd(0) catalytic pathways such as Heck or Suzuki couplings.