20849-84-7

Upstream product

• 187737-37-7 propene 
• 20883-45-8 4-methoxycarbonyl-phenylmercury ⁽¹⁺⁾; chloride 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 107-05-1 3-chloroprop-1-ene 
• 2417-72-3 Methyl 4-(bromomethyl)benzoate 
• 1826-67-1 vinyl magnesium bromide 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 619-44-3 methyl 4-iodobenzoate 
• 106-95-6 allyl bromide 
• 591-87-7 Allyl acetate 
• 619-45-4 4-methoxycarbonyl aniline 
• 762-72-1 allyl-trimethyl-silane 
• 107-18-6 allyl alcohol 
• 24850-33-7 allyltributylstanane 

Downstream Products

• 106918-32-5 4-carbomethoxyphenylacetaldehyde 
• 1093878-06-8 3-(4-(1-hydroxy-1-methylethyl)phenyl)propane-1,2-diol 
• 1093878-07-9 3-[4-(1-hydroxy-1-methylethyl)phenyl]acetaldehyde 
• 106200-41-3 4-(4-carbomethoxyphenyl)butanal 
• 122594-17-6 2-methyl-p-carbomethoxyhydrocinnamic acid 
• 948840-13-9 4-[4-(methoxycarbonyl)phenyl]butanoic acid 

Relevant academic research and scientific papers

Exploiting the trifluoroethyl group as a precatalyst ligand in nickel-catalyzed Suzuki-type alkylations

We report herein the exploitment of the partially fluorinated trifluoroethyl as precatalyst ligands in nickel-catalyzed Suzuki-type alkylation and fluoroalkylation coupling reactions. Compared with the [LnNiII(aryl)(X)] precatalysts, the unique characters of bis-trifluoroethyl ligands imparted precatalyst [(bipy)Ni(CH2CF3)2] with bench-top stability, good solubilities in organic media and interesting catalytic activities. Preliminary mechanistic studies reveal that an eliminative extrusion of a vinylidene difluoride (VDF, CH2CF2) mask from [(bipy)Ni(CH2CF3)2] is a critical step for the initiation of a catalytic reaction.

Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals

In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.

Dual nickel and Lewis acid catalysis for cross-electrophile coupling: The allylation of aryl halides with allylic alcohols

Controlling the selectivity in cross-electrophile coupling reactions is a significant challenge, particularly when one electrophile is much more reactive. We report a general and practical strategy to address this problem in the reaction between reactive and unreactive electrophiles by a combination of nickel and Lewis acid catalysis. This strategy is used for the coupling of aryl halides with allylic alcohols to form linear allylarenes selectively. The reaction tolerates a wide range of functional groups (e.g. silanes, boronates, anilines, esters, alcohols, and various heterocycles) and works with various allylic alcohols. Complementary to most current routes for the C3 allylation of an unprotected indole, this method provides access to C2 and C4-C7 allylated indoles. Preliminary mechanistic experiments reveal that the reaction might start with an aryl nickel intermediate, which then reacts with Lewis acid activated allylic alcohols in the presence of Mn.

Asymmetric Allylic C-H Alkylation via Palladium(II)/ cis-ArSOX Catalysis

We report the development of Pd(II)/cis-aryl sulfoxide-oxazoline (cis-ArSOX) catalysts for asymmetric C-H alkylation of terminal olefins with a variety of synthetically versatile nucleophiles. The modular, tunable, and oxidatively stable ArSOX scaffold is key to the unprecedented broad scope and high enantioselectivity (37 examples, avg. > 90% ee). Pd(II)/cis-ArSOX is unique in its ability to effect high reactivity and catalyst-controlled diastereoselectivity on the alkylation of aliphatic olefins. We anticipate that this new chiral ligand class will find use in other transition metal catalyzed processes that operate under oxidative conditions.

Catalytic Oxidative Trifluoromethoxylation of Allylic C?H Bonds Using a Palladium Catalyst

A catalytic intermolecular allylic C?H trifluoromethoxylation reaction of alkenes has been developed based on the use of a palladium catalyst, CsOCF3 as the trifluoromethoxide source, and benzoquinone as the oxidant. This reaction provides an efficient route for directly accessing allylic trifluoromethoxy derivatives with excellent regioselectivities from terminal alkenes via an allylic C?H bond activation process.

Cross-Coupling Reactions of Aryldiazonium Salts with Allylsilanes under Merged Gold/Visible-Light Photoredox Catalysis

A method for the cross-coupling reactions of aryldiazonium salts with trialkylallylsilanes via merged gold/photoredox catalysis is described. The reaction is proposed to proceed through a photoredox-promoted generation of an electrophilic arylgold(III) intermediate that undergoes transmetalation with allyltrimethylsilane to form allylarenes.

Chemo- and regioselective reductive transposition of allylic alcohol derivatives via iridium or rhodium catalysis

We report highly chemo- and regioselective reductive transpositions of methyl carbonates to furnish olefin products with complementary regioselectivity to that of established Pd-catalysis. These Rh- and Ir-catalysed transformations proceed under mild conditions and enable selective deoxygenation in the presence of functional groups that are susceptible to reduction by metal hydrides.

Alkylations of Arylboronic Acids including Difluoroethylation/Trifluoroethylation via Nickel-Catalyzed Suzuki Cross-Coupling Reaction

An efficient alkylation method of functionalized alkyl halides under mild nickel-catalyzed C(sp3)-(sp2) Suzuki cross-coupling conditions is described. The features of this approach are excellent functional group compatibility, low cost nickel catalyst, and the use of a mild base. This is also the first successful example of the nickel-catalyzed direct 2,2-difluoroethylation or 2,2,2-trifluoroethylation of aryl-/heteroarylboronic acids.

Palladium-catalyzed regioselective azidation of allylic C-H bonds under atmospheric pressure of dioxygen

A palladium-catalyzed allylic azidation of alkenes with sodium azide under atmospheric pressure of dioxygen was developed. This methodology provides a new efficient and simple route for accessing allylic azides. Furthermore, the one-pot process consisting of Pd-catalyzed allylic azidation of alkenes and Cu-catalyzed 1,3-dipolar cycloaddition led directly to the 1,2,3-triazole from the alkene. The formed allylic azide can be also in situ reduced to the allylic amine or oxidized to the alkenyl nitrile. the Partner Organisations 2014.

Cascade multicomponent synthesis of indoles, pyrazoles, and pyridazinones by functionalization of alkenes

The development of multicomponent reactions for indole synthesis is demanding and has hardly been explored. The present study describes the development of a novel multicomponent, cascade approach for indole synthesis. Various substituted indole derivative