30405-75-5

Upstream product

• 74385-18-5 3,4-dimethoxy-(1'-hydroxy-1'-methylethyl)benzene 
• 19493-09-5 Methylenetriphenylphosphorane 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 109125-11-3 <2-(3,4-dimethoxyphenyl)prop-1-en-3-yl>trimethylammonium iodide 
• 50766-67-1 2-(3,4-dimethoxyphenyl)-1,3-dithiane 
• 1206451-03-7 2-(2-bromo-4,5-dimethoxyphenyl)-2-methylpropanal 
• 94824-20-1 1-(3,4-Dimethoxy-phenyl)-aethyl-p-tolyl-sulfon 
• 75-16-1 methylmagnesium bromide 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 67-71-0 dimethylsulfone 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 89980-69-8 3,4-dimethoxyphenylmagnesium bromide 
• 67-64-1 acetone 

Downstream Products

• 92346-00-4 4-((E)-2-Bromo-1-methyl-vinyl)-1,2-dimethoxy-benzene 
• 92345-97-6 4-(1-Bromomethyl-vinyl)-1,2-dimethoxy-benzene 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 40181-01-9 2-(3,4-dimethoxyphenyl)-1-propanol 
• 40181-02-0 Acetic acid 2-(3,4-dimethoxy-phenyl)-propyl ester 
• 1415643-34-3 1,2-dimethoxy-4-(3-tosylprop-1-en-2-yl)benzene 
• 1424343-23-6 2-(3,4-dimethoxyphenyl)prop-2-en-1-ol 
• 1620152-27-3 ethyl (1R,2R)-2-(3,4-dimethoxyphenyl)-2-methylcyclopropanecarboxylate 
• 235417-78-4 3-(3,4-Dimethoxyphenyl)butanal 

Relevant academic research and scientific papers

1,3-Difunctionalization of β-alkyl nitroalkenes via combination of Lewis base catalysis and radical oxidation

Upon treatment with a Lewis base catalyst, β-alkyl-substituted nitroalkenes could be readily converted into allylic nitro compounds. Examples of either C-1 or C-3 functionalization methods have been reported through nitro-elimination, giving alkene products. In this work, successful 1,3-difunctionalization was achieved through a synergetic Lewis base catalysis and TBHP radical oxidation, giving vinylic alkoxyamines in good to excellent yields. This work further extended the general synthetic application of β-alkyl nitroalkenes.

Palladium-Catalyzed Markovnikov Hydroaminocarbonylation of 1,1-Disubstituted and 1,1,2-Trisubstituted Alkenes for Formation of Amides with Quaternary Carbon

Hydroaminocarbonylation of alkenes is one of the most promising yet challenging methods for the synthesis of amides. Herein, we reported the development of a novel and effective Pd-catalyzed Markovnikov hydroaminocarbonylation of 1,1-disubstituted or 1,1,2-trisubstituted alkenes with aniline hydrochloride salts to afford amides bearing an α quaternary carbon. The reaction makes use of readily available starting materials, tolerates a wide range of functional groups, and provides a facile and straightforward approach to a diverse array of amides bearing an α quaternary carbon. Mechanistic investigations suggested that the reaction proceeded through a palladium hydride pathway. The hydropalladation and CO insertion are reversible, and the aminolysis is probably the rate-limiting step.

Ni-Catalyzed Reductive Allylation of α-Chloroboronates to Access Homoallylic Boronates

The transition-metal-catalyzed allylation reaction is an efficient strategy for the construction of new carbon-carbon bonds alongside allyl or homoallylic functionalization. Herein we describe a Ni-catalyzed reductive allylation of α-chloroboronates to efficiently render the corresponding homoallylic boronates, which could be readily converted into valuable homoallylic alcohols or amines or 1,4-diboronates. This reaction features a broad substrate scope with good functional group compatibility that is complementary to the existing methods for the preparation of homoallylic boronates.

Cationic nickel(II)-catalyzed hydrosilylation of alkenes: Role of p, n?type ligand scaffold on selectivity and reactivity

Seven structurally similar cationic nickel(II)?alkyl complexes were synthesized by using a series of P, N ligands, and their reactivity was explored in the hydrosilylation of alkenes. More electron-rich phosphines enhanced the overall reactivity of the transformation; in contrast, groups on the imine donor had little impact. Overall, these catalysts displayed reactivity and selectivity that was previously unknown or very rare in nickel-catalyzed hydrosilylation. In reactions with Ph2SiH2, 1,2-disubstituted vinylarenes showed complete benzylic selectivity for silane addition, whereas terminal selectivity was observed for 1,1-disubstituted alkenes. The related PhSiH3 led to exclusively Markovnikov selectivity for monosubstituted vinylarenes with no competing double addition observed. Mechanistic investigations supported the hypothesis that a Ni?H functions as the active species in this catalytic hydrosilylation, which in turn also showed catalytic competence for the silane redistribution reaction, especially with sterically unhindered silanes.

Single-pot access to bisorganoborinates: Applications in zweifel olefination

Zweifel olefination is a catalyst-free reaction that serves alkene functionalization. While most methods employ commercially available boron pinacol esters, we have assembled a sequence in which the two partners of the formal coupling reaction are installed successively, starting from inexpensive boron alkoxides. The in situ formation of bisorganoborinates was accomplished by consecutive reaction of two different organometallic species. This single-pot procedure represents a great advancement in the generation of organoborinates and their involvement in C-C bond formation.

A convenient access to allylic triflones with allenes and triflyl chloride in the presence of (EtO)2P(O)H

A simple method for the preparation of allylic triflones from allenes and triflyl chloride in the presence of (EtO)2P(O)H has been developed. The features of this reaction are catalyst-free and simple starting substrates. This method tolerates diverse functional groups and substituted allylic triflones are obtained in moderate to good yields.

Nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones with the liberation of H2

A nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones to access various terminal and internal olefins with the liberation of hydrogen gas is reported.

Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: Synthesis of vicinal-dichlorides and chlorodienes

Allyl and vinyl chlorides represent important structural motifs in organic chemistry. Herein is described the chemoselective and regioselective reaction of aryl- and α-substituted phenylallenes with the hypervalent iodine (HVI) reagent 1-chloro-1,2-benz-iodoxol-3-one. The reaction typically results in vicinal dichlorides, except with proton-containing α-alkyl substituents, which instead give chlorinated dienes as the major product. Experimental evidence suggests that a radical mechanism is involved.

Regioselective Copper-Catalyzed Oxidative Coupling of α-Alkylated Styrenes with Tertiary Alkyl Radicals

A radical-mediated oxidative cross-coupling of readily accessible α-alkylated styrenes with 1,3-dicarbonyl compounds utilizing a combination of Cu(OAc)2 and air as a catalytic system is described. Rather than requiring α-halocarbonyl compounds, this efficient approach enables direct installation of tertiary functionalized alkyl motifs to olefins with simple carbonyl derivatives. The novel protocol is characterized with high allylic selectivities via a competing β-H elimination. Both radical-clock and -trapping experiments provided clear-cut evidence for the intermediacy of an α-keto carbon-centered radical.

Fluorinative Rearrangements of Substituted Phenylallenes Mediated by (Difluoroiodo)toluene: Synthesis of α-(Difluoromethyl)styrenes

Phenylallenes undergo fluorinative rearrangement upon the action of (difluoroiodo)toluene in the presence of 20 mol % BF3?OEt2 to yield α-difluoromethyl styrenes. This unprecedented reaction was entirely chemoselective for the internal allene π bond, and showed remarkable regioselectivity during the fluorination event. Substituted phenylallenes, phenylallenes possessing both phenyl- and α-allenyl substituents, and diphenylallenes were investigated, and good functional-group compatibility was observed throughout. The ease with which allenes can be prepared on a large scale, and the operational simplicity of this reaction allowed us to rapidly access fluorine-containing building blocks that have not been accessed by conventional deoxyfluorination strategies.