54582-21-7

Upstream product

• 579-74-8 2-Methoxyacetophenone 
• 13513-82-1 1-(2-methoxyphenyl)ethanol 
• 40023-74-3 1-(2-methoxyphenyl)ethanamine 

Downstream Products

• 111562-31-3 1-(2-methoxy-phenyl)-ethanone-(O-picryl oxime ) 
• 579-74-8 2-Methoxyacetophenone 
• 90-04-0 2-methoxy-phenylamine 
• 725698-74-8 O-(3-amino-5-nitrophenyl)-1-(2-methoxyphenyl)ethanone oxime 
• 29277-46-1 N-(2-methoxyphenyl)ethanethioamide 
• 1257846-22-2 (E)-1-(2-methoxyphenyl) ethanone O-acetyl oxime 
• 1257846-37-9 1-methyl-3,4-diphenyl-8-methoxy-isoquinoline 
• 1244768-86-2 (E)-N-(1-(1H-benzo[d][1,2,3]triazol-1-yl)ethylidene)-2-methoxyaniline 
• 93-26-5 2-methoxyacetanilide 
• 536717-77-8 O-(tert-butyldimethylsilyl)-2-methoxyacetophenone oxime 
• 40023-74-3 1-(2-methoxyphenyl)ethanamine 
• 95-21-6 2-methyl-1,3-benzoxazole 
• 1434602-23-9 (E)-1-(2-methoxyphenyl)ethanone O-benzyloxime 
• 40023-74-3 (S)-1-(2-methoxyphenyl)ethanamine 

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.

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.

Chlorotropylium Promoted Conversions of Oximes to Amides and Nitriles

Chlorotropylium chloride as a catalyst for the transformations of oximes, ketones, and aldehydes to their corresponding amides and nitriles in excellent yields (up to 99 %) and in short reaction times (mostly 10–15 min). Oximes were electrophilically attacked on the hydroxyl oxygen by chlorotropylium. The produced tropylium oxime ethers were the key intermediates, of which the ketoxime ether led to amide through Beckmann rearrangement, and the aldoxime ether led to nitrile by nitrogen base DBU assisted formal dehydration. This chlorotropylium activation protocol offered general, mild, and efficient avenues bifurcately from oximes to both amides and nitriles by one organocatalyst.

Direct Enamido C(sp2)?H Diphosphorylation Enabled by a PCET-Triggered Double Radical Relay: Access to gem-Bisphosphonates

Herein we report a novel and straightforward protocol for the construction of valuable gem-BPs by means of proton-coupled electron-transfer (PCET)-triggered enamido C(sp2)?H diphosphorylation. This reaction represents a rare example of realizing the challenging double C?P bond formation at a single carbon atom, thus providing facile access to a broad variety of structurally diverse bisphosphonates from simple enamides under silver-mediated conditions. Initial mechanistic studies demonstrated that the diphosphorylation involves two rounds of PCET-initiated radical relay process.

Merging alkenyl C-H activation with the ring-opening of 1,2-oxazetidines: Ruthenium-catalyzed aminomethylation of enamides

1,2-Oxazetidines have been utilized as formaldimine precursors for the direct aminomethylation of enamides under a Ru(ii) species. By merging alkenyl C-H activation with ring-opening of 1,2-oxazetidines, this efficient protocol provides a facile and novel

Cu(OTf) 2 -Catalyzed Beckmann Rearrangement of Ketones Using Hydroxylamine- O -sulfonic Acid (HOSA)

The Beckmann rearrangement (BKR) of ketones to secondary amides often requires harsh reaction conditions that limit its practicality and scope. Herein, the Cu(OTf) 2 -catalyzed BKR of ketones under mild reaction conditions using hydroxylamine- O -sulfonic acid (HOSA), a commercial water soluble aminating agent, is described. This method is compatible with most functional groups and directly provides the desired amides in good to excellent yields.

SO2F2-Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams

A novel, mild and practical protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available and economical sulfuryl fluoride (SO2F2 gas) has been developed. The substrate scope of the operationally simple methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields (over 90 % yield in most cases) in a short time, including B(OH)2, COOH, NH2, and OH substituted substrates. A tentative mechanism was proposed involving formation and elimination of key intermediate, sulfonyl ester.

Rhodium(III)-Catalyzed Annulation of Acetophenone O-Acetyl Oximes with Allenoates through Arene C-H Activation: An Access to Isoquinolines

Rhodium(III)-catalyzed annulation of acetophenone O-acetyl oximes with allenoates was achieved, affording isoquinolines in good to excellent yields with high regioselectivities under redox-neutral conditions. Allenoates acted as the C2 synthons in the annulation reaction. The present synthetic methodology features good functional group tolerance and avoids metal salts as the external oxidants. The proposed mechanism suggests that the reaction proceeds through arene C-H activation, allene insertion, and C-N coupling.

Visible Light-Promoted Beckmann Rearrangements: Separating Sequential Photochemical and Thermal Phenomena in a Continuous Flow Reactor

The Beckmann rearrangement of oximes to amides typically requires strong acids or highly reactive, hazardous electrophiles and/or elevated temperatures to proceed. A very attractive alternative is the in situ generation of Vilsmeier–Haack reagents, by means of photoredox catalysis, as promoters for the thermal Beckmann rearrangement. Investigation of the reaction parameters for this light-induced method using a one-pot strategy has shown that the reaction is limited by the different temperatures required for each of the two sequential steps. Using a continuous flow reactor, the photochemical and thermal processes have been separated by integrating a flow photoreactor unit at low temperature for the electrophile generation with a second reactor unit, at high temperature, where the rearrangement takes place. This strategy has enabled excellent conversions and yields for a diverse set of oximes, minimizing the formation of side products obtained with the original one-pot method.

Direct access to bis-S-heterocycles via copper-catalyzed three component tandem cyclization using S8 as a sulfur source

A novel strategy for constructing sulfur containing bis-S-heterocyclic compounds from oxime esters/vinyl azide, phenylacetylene/aldehydes and elemental sulfur (S8) has been developed. These transformations show good functional group tolerance. Various bis-S-heterocyclic products were efficiently synthesized from easily prepared or widely commercially available starting materials. In this protocol, S8 successfully served as a two-sulfur atom donor for thiophene and thiazole rings, respectively.