329-79-3

Usage

Chemical Properties

White to slightly yellow needles

InChI:InChI=1/C8H8FNO/c1-6(10-11)7-2-4-8(9)5-3-7/h2-5,11H,1H3/b10-6-

Upstream product

• 107093-07-2 1-(4-Fluoro-phenyl)-1-hydroxyamino-ethanol 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 546-88-3 acetylhydroxamic acid 
• 99-91-2 para-chloroacetophenone 
• 79-24-3 Nitroethane 
• 462-06-6 fluorobenzene 

Downstream Products

• 524-27-6 1-(4-fluoro-phenyl)-ethanone-((E)-O-picryl oxime ) 
• 405-67-4 ethyl-(4-fluoro-phenyl)-amine 
• 403-40-7 1-(4-fluorophenyl)ethylamine 
• 31709-51-0 3-(4-fluorophenyl)isoxazol-5 (4H)-one 
• 748771-34-8 3-(4-Fluorophenyl)-5-(4-hydroxyphenyl)isoxazole 
• 119830-49-8 2-(4-fluorophenyl)-5-methyl-1H-pyrrole 
• 79039-69-3 6-chloro-2-(4-fluorophenyl)-4-phenylquinoline 
• 110319-94-3 2-(4-fluorophenyl)-1H-pyrrole 
• 351-83-7 4'-fluoroacetanilide 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 491875-99-1 3-(4-fluoro-phenyl)-5-methylisoxazole 
• 491876-00-7 4-bromo-3-(4-fluorophenyl)-5-methyl-isoxazole 

Relevant academic research and scientific papers

Polysubstituted Indole Synthesis via Palladium/Norbornene Cooperative Catalysis of Oxime Esters

Polysubstituted indoles are prevalent in pharmaceuticals, agrochemicals, and organic materials. Presented herein is the fact that polyfunctionalized indoles can be efficiently constructed from easily accessible oxime esters and aryl iodides, involving a palladium/norbornene synergistic synthesis. The reaction is enabled by a unique class of electrophiles in palladium/norbornene cooperative catalysis, which are oxime esters derived from simple ketone. The broad substrate scope and high functional group tolerance could make this method attractive for the synthesis of polysubstituted indoles.

AgNO3as Nitrogen Source for Cu-Catalyzed Cyclization of Oximes with Isocyanates: A Facile Route to N-2-Aryl-1,2,3-triazoles

A versatile copper-catalyzed [3 + 1 + 1] annulation of oximes and isocyanates with AgNO3 is described. In this conversion, AgNO3 and isocyanates instead of conventional azide or diazonium reagents were used as the nitrogen source. This three-component transformation was achieved by cleaving N-O/C-H/C-N bonds and building CN/N-N bonds, which provides a strategy to prepare N-2-aryl-1,2,3-triazoles with a good substrate and functional compatibility.

Access to multi-functionalized oxazolines via silver-catalyzed heteroannulation of enamides with sulfoxonium ylides

Disclosed herein is an efficient Ag-catalyzed [4 + 1] heteroannulation reaction of enamides with α-carbonyl sulfoxonium ylides. The diastereoselective transformation provides a practical access to a diverse range of multi-functionalized oxazoline derivatives. The synthetic utility of the resultant tetra-substituted oxazolines is further demonstrated by a series of useful manipulations into valuable building blocks of pharmaceutical relevance.

Rhodium(III)-Catalyzed Direct C-H Arylation of Various Acyclic Enamides with Arylsilanes

The stereoselective β-C(sp2)-H arylation of various acyclic enamides with arylsilanes via Rh(III)-catalyzed cross-coupling reaction was illustrated. The methodology was characterized by extraordinary efficacy and stereoselectivity, a wide scope of substrates, good functional group tolerance, and the adoption of environmentally friendly arylsilanes. The utility of this present method was evidenced by the gram-scale synthesis and further elaboration of the product. In addition, Rh(III)-catalyzed C-H activation is considered to be the critical step in the reaction mechanism.

Visible-light-promoted olefinic trifluoromethylation of enamides with CF3SO2Na

A visible-light-promoted olefinic C-H trifluoromethylation of enamides was developed by employing cheap and stable Langlois’ reagent as the CF3source. A series of β-CF3enamides were obtained in moderate to good yields with highE-isomer selectivity under mild conditions. Preliminary mechanistic studies suggest that molecular oxygen acts as the terminal oxidant for this net oxidative process, and theEisomer selectivity could be well explained by a base-assisted deprotonation of the cation intermediate.

Rhodium-Catalyzed C?H Activation/Annulation Cascade of Aryl Oximes and Propargyl Alcohols to Isoquinoline N-Oxides

A β-hydroxy elimination instead of common oxidization to carbonyl group in secondary propargyl alcohols was successfully developed to form 2-benzyl substituted isoquinoline N-oxides by a Rhodium-catalyzed C?H activation and annulation cascade, in which moderate to excellent yields (up to 92%) could be obtained under mild reaction conditions, along with good regioselectivity, broad generality and applicability. (Figure presented.).

Rhodium(iii)-catalyzed asymmetric [4+1] spiroannulations of: O -pivaloyl oximes with α-diazo compounds

Chiral RhIII catalysts can catalyze the asymmetric [4+1] spiroannulation of O-pivaloyl oximes with α-diazo homophthalimides under redox-neutral and acid/base-neutral conditions, leading to formation of chiral spirocyclic imines as a result of C-H activation and N-O cleavage. The reaction proceeded with high efficiency and features broad substrate scope, mild reaction conditions, and high to excellent enantioselectivities. This journal is

Selective Dehydrogenative Acylation of Enamides with Aldehydes Leading to Valuable β-Ketoenamides

We have presented a unique example of dehydrogenative acylation of enamides with aldehydes enabled by an earth-abundant iron catalyst. The protocol provides the straightforward access to valuable β-ketoenamides with ample substrate scope and excellent functional group tolerance. Notably, distinct C-H acylation of enamide rather than at N-H moiety site occurs with absolute Z-selectivity was observed. Late-stage modifications of complex molecules and versatile synthetic utility of β-ketoenamides further highlight the practicability of this transformation.

Synthesis of Functionalized Vinylsilanes via Metal-Free Dehydrogenative Silylation of Enamides

A novel method of metal-free dehydrogenative silylation of enamides has been developed. The desired functionalized vinylsilane products were obtained in moderate to good yield and with high stereoselectivities. This protocol displays good tolerance of various functionalities. Furthermore, the high chemoselectivity of this reaction enables us to introduce different unsaturated C-C moieties to the products. The ease of further derivatization of the products to other useful compounds also demonstrates the highly synthetic utility of the current methodology.

Arylboronic Acid-Catalyzed C-Allylation of Unprotected Oximes: Total Synthesis of N-Me-Euphococcine

O-Unprotected keto-and aldoximes are readily C-allylated with allyl diisopropyl boronate in the presence of arylboronic acid catalysts to yield highly substituted N-α-secondary and tertiary homoallylic hydroxylamines. The method was used in the total synthesis of the trace alkaloid N-Me-Euphococcine.