5448-36-2

Usage

InChI:InChI=1/C14H21NO/c1-10(2)15(11(3)4)14(16)13-8-6-7-12(5)9-13/h6-11H,1-5H3

Upstream product

• 4294-57-9 para-methylphenylmagnesium bromide 
• 155496-73-4 2-(tert-butylsulfonyl)-N,N-diisopropyl-5-methylbenzamide 
• 20383-28-2 N,N-diisopropyl benzamide 
• 161431-82-9 2-tert-Butylsulfanyl-N,N-diisopropyl-benzamide 
• 155496-72-3 2-(tert-butylsulfonyl)-N,N-diisopropylbenzamide 
• 108-18-9 diisopropylamine 
• 1711-06-4 3-Methylbenzoyl chloride 
• 99-04-7 m-Toluic acid 

Downstream Products

• 1351765-32-6 (E)-5-methyl-2-(prop-1-enyl)benzoic acid 
• 1351765-14-4 3-methyl-N,N-diisopropyl-2-formylbenzamide 
• 1351765-11-1 5-methyl-N,N-diisopropyl-2-formylbenzamide 
• 72288-75-6 3-hydroxy-4-methylisobenzofuran-1(3H)-one 
• 177166-16-4 3-hydroxy-6-methylisobenzofuran-1(3H)-one 
• 1375931-09-1 2-bromo-N,N-diisopropyl-5-methylbenzamide 
• 1392473-20-9 2-hydroxy-N,N-diisopropyl-5-methylbenzamide 
• 1557179-00-6 2-cyano-N,N-diisopropyl-5-methylbenzamide 
• 1527480-00-7 (2-iodo-3,5-dimethylphenyl)(piperidin-1-yl)methanone 
• 34665-58-2 6-methyl-2,3-diphenyl-1H-inden-1-one 
• 20359-57-3 1-(3-methylphenyl)pentan-1-one 

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.

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

An efficient method for the preparation of styrene derivatives via Rh(III)-catalyzed direct C-H vinylation

The development of a method for the Rh(III)-catalyzed direct vinylation of an aromatic C-H bond to give functionalized styrenes in good yield, using vinyl acetate as a convenient and inexpensive vinyl source, is reported. High functional group tolerance is demonstrated for electronically distinct arenes as well as different directing groups. Mechanistic investigation resulted in the characterization of a novel rhodium-metallacycle, which represents the first X-ray structure of a [1,2]-Rh(III)-alkenyl addition adduct.

Rhodium-catalyzed direct coupling of benzothioamides with alkenes and alkynes through directed C-H bond cleavage

Rhodium-catalyzed direct coupling of benzothioamides with alkenes proceeds smoothly involving ortho-CH bond cleavage. The thioamides also couple with alkynes under similar conditions accompanied by desulfurization and CN bond cleavage to produce indenone derivatives.

Ruthenium-catalyzed ortho-C-H halogenations of benzamides

[Ru3(CO)12] and AgO2C(1-Ad) enabled the first ruthenium-catalyzed intermolecular halogenations of arenes via C-H activation. Thereby, brominations and iodinations of electron-rich and electron-deficient benzamides were ach

Regioselective Pd-catalyzed aerobic aza-Wacker cyclization for preparation of isoindolinones and isoquinolin-1(2 H)-ones

A switchable regioselective intramolecular aerobic aza-Wacker cyclization catalyzed by palladium is presented. Isoindolinones or isoquinolin-1(2H)-ones could be prepared selectively from the same substrates using different catalysts. The type and steric hindrance of the ligands may be the variables most significant for regiocontrol.

[RhIIIcp*]-catalyzed dehydrogenative aryl-aryl bond formation

Directed, undirected! Rhodium(III)-catalyzed double CH bond activation (one directed, one undirected) provides an efficient route to biaryls (see scheme; DG=directing group). Significant kinetic isotope effects for both reaction partners and H/D scrambling between them are interesting experimental findings. While the mechanism is still unclear, a rhodium(V) species is invoked in the catalytic cycle. Copyright

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.

Nickel-catalysed Substitutions of Aryl tert-Butyl Sulfones with Organometallic Reagents: Synthesis of ortho-Substituted Unsymmetrical Biaryls

In the presence of a catalytic amount of a nickel salt, aryl tert-butyl sulfones react with aryl Grignard reagents to give biaryls.This reaction is used in conjunction with the powerful ortho-lithiation-directing ability of aryl tert-butyl sulfonyl groups to make unsymmetrical ortho-substituted biaryls.In certain cases, the substitution of an aryl alkylsulfonyl group by an organometallic reagent is possible without a transition metal catalyst.

ortho-Substituted Unsymmetrical Biaryls from Aryl tert-Butyl Sulfones

Nickel-catalysed coupling of arylmagnesium halides with aryl tert-butyl sulfones, and in particular with those bearing ortho-substituents introduced by ortholithiation, gives ortho-substituted unsymmetrical biaryls.