82573-53-3

Upstream product

• 98-88-4 benzoyl chloride 
• 585-32-0 2-phenyl-2-propylamine 
• 55-21-0 benzamide 
• 98-83-9 isopropenylbenzene 
• 32366-26-0 cumyl azide 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 98-82-8 Isopropylbenzene 
• 582-61-6 benzoyl azide 
• 826-54-0 2-methyl-2-phenyl-propanamide 
• 93-97-0 benzoic acid anhydride 
• 3575-19-7 2-bromo-2-phenylpropane 
• 300561-20-0 N-benzoyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamide 

Downstream Products

• 249764-80-5 C₁₇H₁₉NOS 
• 249764-82-7 2-iodo-N-(2-phenyl-2-propyl)benzamide 
• 249764-77-0 C₁₇H₁₇NO₂ 
• 249764-72-5 N-(2-phenylpropan-2-yl)-2-(trimethylsilyl)benzamide 
• 249764-70-3 3-hydroxy-2-(1-methyl-1-phenylethyl)-2,3-dihydro-1H-isoindol-1-one 
• 249764-83-8 C₂₃H₂₃NO 
• 249764-88-3 C₁₈H₁₉NO₂S 
• 249764-89-4 C₂₀H₂₃NO₂Si 
• 249764-90-7 C₁₈H₁₇NO₂S 
• 249764-91-8 C₂₀H₂₀N₂O₃ 
• 54705-16-7 2-methylsulfanyl-benzamide 
• 17876-72-1 2-(trimethylsilyl)benzamide 
• 86863-90-3 2-(trimethylsilyl)benzonitrile 

Relevant academic research and scientific papers

Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium

Isoselenazolone derivatives have attracted significant research interest because of their potent therapeutic activities and indispensable applications in organic synthesis. Efficient construction of functionalized isoselenazolone scaffolds is still challenging, and thus new synthetic approaches with improved operational simplicity have been of particular interest. In this manuscript, we introduce a rhodium-catalyzed direct selenium annulation by using stable and tractable elemental selenium. A series of benzamides as well as acrylamides were successfully coupled with selenium under mild reaction conditions, and the obtained isoselenazolones could be pivotal synthetic precursors for several organoselenium compounds. Based on the designed control experiments and X-ray absorption spectroscopy measurements, we propose an unprecedented selenation mechanism involving a highly electrophilic Se(IV) species as the reactive selenium donor. The reaction mechanism was further verified by a computational study.

Copper-Catalyzed C(sp3)?H Amidation: Sterically Driven Primary and Secondary C?H Site-Selectivity

Undirected C(sp3)?H functionalization reactions often follow site-selectivity patterns that mirror the corresponding C?H bond dissociation energies (BDEs). This often results in the functionalization of weaker tertiary C?H bonds in the presence of stronger secondary and primary bonds. An important, contemporary challenge is the development of catalyst systems capable of selectively functionalizing stronger primary and secondary C?H bonds over tertiary and benzylic C?H sites. Herein, we report a Cu catalyst that exhibits a high degree of primary and secondary over tertiary C?H bond selectivity in the amidation of linear and cyclic hydrocarbons with aroyl azides ArC(O)N3. Mechanistic and DFT studies indicate that C?H amidation involves H-atom abstraction from R-H substrates by nitrene intermediates [Cu](κ2-N,O-NC(O)Ar) to provide carbon-based radicals R. and copper(II)amide intermediates [CuII]-NHC(O)Ar that subsequently capture radicals R. to form products R-NHC(O)Ar. These studies reveal important catalyst features required to achieve primary and secondary C?H amidation selectivity in the absence of directing groups.

Ortho-directed functionalization of arenes using magnesate bases

Ortho-directed functionalisation of arenes using lithium alkylmagnesate bases were achieved, demonstrating the potential use of arylmagnesates as suitable arylanions, without a further transmetallation step, for challenging functionalizations such as fluorination, hydroxylation, arylation, vinylation and alkylation through epoxide ring-opening.

Behaviour of N-pyridylbenzamides versus benzanilides in the ortho-directed lithiation of masked aromatic carboxylic acids

The reaction of N-pyridylbenzamides 1-3 with n-butyllithium or sec-butyllithium has been examined. The perfect selectivity that has been observed until now in the lithiation of anilides, a reaction used for ortho-functionalisation of masked aromatic carboxylic acids, has been broken; our results indicate that the pyridine ring at the position ortho to the directed metallation group is more susceptible to lithiation than the homoaromatic ring itself. This was proved in an intermolecular comparative study of benz-, picolin- and isonicotinanilides 14-16, and N-cumylbenzamide (17). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Studies on development of sufficiently chemoselective N-acylation reagents: N-Acyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamides

A variety of storable N-acyl-N-(2,3,4,5,6-pentafluorophenyl)methanesulfonamides (4a-e) prepared from N-2,3,4,5,6-pentafluorophenylmethanesulfonamide (3), have been developed after systematic research on the structure-reactivity relationship and were found to serve as N-acylation reagents exhibiting sufficiently good chemoselectivity. (C) 2000 Elsevier Science Ltd.

N-cumyl benzamide, sulfonamide, and aryl O-carbamate directed metalation groups. Mild hydrolytic lability for facile manipulation of directed ortho metalation derived aromatics

(Matrix Presented) N-Cumyl benzamide (2), sulfonamide (8), and O-carbamate (11) compounds undergo directed ortho metalation under standard conditions to give, after quench with a variety of electrophiles, the substituted products 3, 9, and 12, respectively. Regiospecific and convenient approaches to phthalimides (7), 1,2-benzisothiazole 1,1-dioxides (10b), and ortho-substituted phenols (13a) and salicylamides (13b) are thereby established The mild deprotection protocol for these new cumyl directed metalation groups (DMGs) suggests that they will supersede previous corresponding groups for synthetic anionic aromatic chemistry.

2-chloro-N,N-dibenzoylaniline: A selective N-benzoylating reagent

Highly selective benzoylation of a less hindered amino group in the presence of a more hindered amino group with 2-chloro-N,N-dibenzoylaniline (2d), a convenient to use and stable reagent, is described.

Amidomercuriation: A General Addition of Amides and Related Compounds to Olefins

The addition of different carboxamides and related compounds such as urethane or urea to olefins using mercury(II) nitrate followed by sodium borohydride reduction to give the corresponding N-substituted amides, urethanes, or ureas, respectively, is described.The monoalkylated ureas, through the same amidomercuriation-demercuriation procedure, yield symmetrical and unsymmetrical N,N'-disubstituted ureas.This amidomercuriation-demercuriation process provides a new, convenient, and general method for the Markovnikov amidation of carbon-carbon double bonds.