86718-78-7

Upstream product

• 556-56-9 allyl iodid 
• 459-57-4 4-fluorobenzaldehyde 
• 1730-25-2 allylmagnesium bromide 
• 4180-01-2 bis(allyldimethylsilyl)methane 
• 156578-45-9 o-bis(allyldimethylsilyl)benzene 
• 107-05-1 3-chloroprop-1-ene 
• 762-72-1 allyl-trimethyl-silane 
• 191732-48-6 (E)-(3-bromoprop-1-en-1-yl)tributylstannane 
• 591-87-7 Allyl acetate 
• 107-18-6 allyl alcohol 
• 106-95-6 allyl bromide 
• 107-37-9 allyltrichlorosilane 
• 459-56-3 4-fluorobenzylic alcohol 
• 613-94-5 benzoic acid hydrazide 

Downstream Products

• 865776-83-6 3-(4-fluoro-phenyl)-3-methoxy-propionaldehyde 
• 865777-01-1 5-[2-(4-fluoro-phenyl)-2-methoxy-ethyl]-thiazole-4-carboxylic acid methyl ester 
• 865777-10-2 5-[2-(4-fluoro-phenyl)-2-methoxy-ethyl]-thiazole-4-carboxylic acid 
• 865776-92-7 2-amino-5-[2-(4-fluoro-phenyl)-2-methoxy-ethyl]-thiazole-4-carboxylic acid methyl ester 
• 136185-89-2 1-(4-fluorophenyl)-3-butenyl N,N-bis(2-chloroethyl)phosphorodiamidate 
• 129253-34-5 cis-2--4-hydroperoxy-6-(4-fluorophenyl)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide 
• 1210066-87-7 (E)-4-(4-fluorophenyl)-4-hydroxybut-2-enyl propionate 
• 1210066-89-9 (E)-4-(4-fluorophenyl)-4-hydroxybut-2-enyl pivalate 
• 677004-14-7 1-(4-fluorophenyl)but-3-en-1-yl acetate 
• 253443-43-5 5-(chloromethyl)-3-(4-fluorophenyl)-4,5-dihydroisoxazole 
• 1158557-09-5 5-benzyl-3-(4-fluorophenyl)-2-Δ²-isoxazoline 

Relevant academic research and scientific papers

Palladium-catalyzed anti-Markovnikov oxidative acetalization of activated olefins with iron(iii) sulphate as the reoxidant

This paper discloses the efficient palladium-catalyzed anti-Markovnikov oxidative acetalization of activated terminal olefins with iron(iii) sulfate as the reoxidant. This methodology requires mild reaction conditions and shows high regioselectivity toward anti-Markovnikov products and compatibility with a wide range of functional groups. Iron(iii) sulphate was the sole reoxidant used in this method. Various olefins like vinylarenes, aryl-allylethers, aryl or benzyl acrylates and homoallylic alcohols all reacted well providing anti-Markovnikov acetals, some of which represent orthogonally functionalized 1,3- and 1,4-dioxygenated compounds.

Organocatalytic Asymmetric Synthesis of Cyclic Acetals with Spirooxindole Skeleton

An organocatalytic asymmetric synthesis of cyclic acetal with spirooxindole skeleton has been developed via a domino reaction between isatin and γ-hydroxy enones. Bifunctional squaramide catalyst with adamantyl motif was found to be the most effective for the cascade reaction. With 10 mol% of the catalyst, the desired products were obtained in 1.8:1 to 9:1 diastereo- and 86% to >99% enantioselectivities from a range of substituted isatins and γ-hydroxy enones. (Figure presented.).

Visible Light-Promoted Recyclable Carbon Nitride-Catalyzed Dioxygenation of β,γ-Unsaturated Oximes

A visible-light-induced dioxygenation of β,γ-unsaturated oximes for the synthesis of diverse useful isoxazolines bearing a hydroxyl moiety was developed by employing graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst under an air atmosphere. Noted that, the eminent advantages of this metal-free protocol include step economy, easy operation, a recyclable photocatalyst, external reductant-/oxidant-free and mild reaction conditions. Additionally, mechanistic studies indicated hydroxyl radical was generated under the photocatalysis of g-C3N4.

Photoredox Allylation Reactions Mediated by Bismuth in Aqueous Conditions

Organometallic allylic reagents are widely used in the construction of C?C bonds by Barbier-type reactions. In this communication, we have described a photoredox Barbier allylation of aldehydes mediated by bismuth, in absence of other metals as co-reductants. Mild reaction conditions, tolerance of oxygen, and use of aqueous solvent make this photoredox methodology attractive for green and sustainable synthesis of homoallylic alcohols.

Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines

A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.

Ni-Catalyzed 1,2-Diarylation of Alkenyl Ketones: A Comparative Study of Carbonyl-Directed Reaction Systems

A nickel-catalyzed 1,2-diarylation of alkenyl ketones with aryl iodides and arylboronic esters is reported. Ketones with a variety of substituents serve as effective directing groups, offering high levels of regiocontrol. A representative product is diversified into a wide range of useful products that are not readily accessible via existing 1,2-diarylation reactions. Preliminary mechanistic studies shed light on the binding mode of the substrate, and Hammett analysis reveals the effect of electronic factors on initial rates.

Catalytic Photoredox Allylation of Aldehydes Promoted by a Cobalt Complex

The preparation of homoallylic alcohols by addition of organometallic allyl compounds to carbonyls is an important strategy in organic chemistry. Allylating organometallic cobalt species can be generated employing stoichiometric quantities of Zn acting as reductant. To avoid the employment of stoichiometric amount of Zn, we have developed an allylation reaction of aromatic and aliphatic aldehydes promoted by photoredox catalysis in the presence of a cobalt complex, and we present herein a full account of our research. In the presence of the abundant CoBr2 (10 mol %), 4,4′-di-tert-butyl-2,2′-dipyridyl (dtbbpy, 10 mol %), allyl acetate (3 equiv.), [Ir(dtbbpy)(ppy)2]PF6 (ppy=2-phenylpyridine, 2 mol %), and N,N-diisopropylethylamine (4 equiv.), an allylation of aldehydes is taking place, in moderate to good yields. Substrates scope, limitations, and photophysical investigations of this new process are reported. (Figure presented.).

Nickel-Catalyzed Reductive Allylation of Aldehydes with Allyl Acetates

Carbonyl allylation reactions constitute an important step in the formation of carbon-carbon reactions, and involve various related reactions that chiefly use allylmetal reagents. This report presents a nickel-catalyzed carbonyl allylation reaction using allyl acetate, which produces homoallyl alcohols in moderate to good yields, as an efficient methodology under reductive coupling conditions.

Photocatalytic Umpolung Synthesis of Nucleophilic π-Allylcobalt Complexes for Allylation of Aldehydes

The concept of "umpolung"reactivity of π-allylmetal complexes has been developed as a powerful method for the allylation of aldehydes. This paper describes the photocatalytic umpolung strategy for the synthesis of nucleophilic allylcobalt complexes through a single-electron-transfer (SET) process. This strategy enables the metallaphotoredox allylation of carbonyls with allyl acetate using organic N,N-diisopropylethylamine as the terminal reductant bypassing the use of a stoichiometric amount of metals. Ultraviolet-visible spectroscopy was used to monitor the redox changes of cobalt in the reaction.

Photoinduced Olefin Diamination with Alkylamines

Vicinal diamines are ubiquitous materials in organic and medicinal chemistry. The direct coupling of olefins and amines would be an ideal approach to construct these motifs. However, alkene diamination remains a long-standing challenge in organic synthesis, especially when using two different amine components. We report a general strategy for the direct and selective assembly of vicinal 1,2-diamines using readily available olefin and amine building blocks. This mild and straightforward approach involves in situ formation and photoinduced activation of N-chloroamines to give aminium radicals that enable efficient alkene aminochlorination. Owing to the ambiphilic nature of the β-chloroamines produced, conversion into tetra-alkyl aziridinium ions was possible, thus enabling diamination by regioselective ring-opening with primary or secondary amines. This strategy streamlines the preparation of vicinal diamines from multistep sequences to a single chemical transformation.