5448-58-8

Upstream product

• 615-37-2 ortho-methylphenyl iodide 
• 201230-82-2 carbon monoxide 
• 109-73-9 N-butylamine 
• 95-46-5 2-methylphenyl bromide 
• 933-88-0 ortho-toluoyl chloride 
• 19798-58-4 N-chloro-n-butylamine 
• 529-20-4 2-methylphenyl aldehyde 
• 13939-06-5 molybdenum hexacarbonyl 
• 89-95-2 2-methyl-benzyl alcohol 
• 609-67-6 2-Iodobenzoyl chloride 
• 95-47-6 o-xylene 
• 118-90-1 ortho-methylbenzoic acid 

Downstream Products

• 1391997-33-3 C₁₃H₁₉NO 

Relevant academic research and scientific papers

Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation

The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.

Radical-mediated divergent cyclization of benzamides toward perfluorinated or cyanated isoquinolinediones

A simple and efficient copper-controlled divergent cyclization of benzamides, which leads to perfluorinated or cyanated isoquinolinediones, is developed. In the presence of AIBN, methacryloyl benzamides with perfluoroalkyl iodides undergo cascade radical addition/cyclization to afford perfluoroinated isoquinolinediones as the major product under metal-free conditions, whereas the use of CuI (10 mol%) is able to redirect the cyclization to yield isoquinolinediones bearing an α-cyano quaternary carbon center. The cyclization features controllable divergent synthesis and a broad substrate scope as well as highly practical reaction conditions, thereby making this strategy a highly attractive means to fluorinate or cyanate isoquinolinediones.

Direct oxidative amidation between methylarenes and amines in water

An environmentally friendly direct oxidative amidation between methylarenes and free amines was developed. The aromatic amide could be prepared efficiently from raw chemicals by employing TBHP as a "green" oxidant with co-catalysis of TBAI and FeCl3 in water.

Halocarbocyclization versus dihalogenation: Substituent directed iodine(iii) catalyzed halogenations

The nucleophilicity of the substituents in iodobenzene pre-catalysts have a huge impact on product selectivity in iodine(iii) triggered halogenations, steering the reactivity from solely carbocyclizations towards dihalogenations. Utilizing this catalyst-dependent reactivity a diastereo- and chemoselective dihalogenation method was established allowing the conversion of structurally and electronically diverse unsaturated compounds in excellent yields.

The First ZnII-Catalyzed Oxidative Amidation of Benzyl Alcohols with Amines under Solvent-Free Conditions

The first zinc-catalyzed oxidative amidation of benzyl alcohols has been developed. Both aliphatic and aromatic amines can be tolerated and applied in this reaction. Various amides were prepared in good yields under solvent-free and mild conditions. Copyright

Intramolecular C(sp3)-N coupling by oxidation of benzylic C,N-dianions

What a couple! An intramolecular, C(sp3)-N coupling to afford azacycles is reported. This reaction proceeds through the oxidation of benzylic C,N-dianions with iodine and builds on an earlier discovery during the synthesis of the natural produc

A copper-catalysed amidation of aldehydes via N-hydroxysuccinimide ester formation

A copper-catalysed oxidative amidation of aldehydes via N-hydroxysuccinimide ester formation is reported. The methodology employed to prepare amides directly from aldehydes has a very wide scope, is high yielding, and does not need dry conditions. This cross-coupling reaction appears to be simple and makes use of cheap, abundant and easily available reagents.

Aminocarbonylations employing Mo(CO)6 and a bridged two-vial system: Allowing the use of nitro group substituted aryl iodides and aryl bromides

A bridged two-vial system aminocarbonylation protocol where Mo(CO) 6 functions as an external in situ solid source of CO has been developed. For the first time both nitro group containing aryl/heteroaryl iodides and bromides gave good to excellent yields in the Mo(CO) 6-mediated and palladium(0)-catalyzed conversion to benzamides, while the identical one-vessel protocol afforded extensive reduction of the nitro functionality. The above-mentioned bridged two-compartment protocol furnished good results with both primary amines and secondary amines and sluggish aniline nucleophiles at 65-85 C reaction temperatures.

High-yielding, versatile, and practical [Rh(III)Cp*]-catalyzed ortho bromination and iodination of arenes

We report a uniquely high-yielding, general, and practical ortho bromination and iodination reaction of different classes of aromatic compounds. This reaction occurs by Rh(III)-catalyzed C-H bond activation methodology and is therefore the first example of the application of this cationic catalyst for C-Br and C-I bond formation.

A phosphine-free Pd catalyst for the selective double carbonylation of aryl iodides

The first phosphine-free Pd-catalysed double carbonylation of aryl iodides is reported as a general and practical method, giving excellent conversions and selectivities for a wide range of aryl iodides and amine nucleophiles under atmospheric CO pressure. The Royal Society of Chemistry 2012.