82746-16-5

Upstream product

• 75802-22-1 1-ethoxyisochromane 
• 70-55-3 toluene-4-sulfonamide 
• 493-05-0 isochromane 
• 7080-50-4 chloramine-T hydrate 
• 95033-78-6 1-hydroxyisochroman 
• 21849-40-1 dibromamine-T 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 

Downstream Products

• 36808-38-5 N-[2-(2-Hydroxy-ethyl)-benzyl]-4-methyl-benzenesulfonamide 

Relevant academic research and scientific papers

A Metal–Organic Framework with Exceptional Activity for C?H Bond Amination

The development of catalysts capable of fast, robust C?H bond amination under mild conditions is an unrealized goal despite substantial progress in the field of C?H activation in recent years. A Mn-based metal–organic framework (CPF-5) is described that promotes the direct amination of C?H bonds with exceptional activity. CPF-5 is capable of functionalizing C?H bonds in an intermolecular fashion with unrivaled catalytic stability producing >105 turnovers.

Organocatalytic nitrenoid transfer: Metal-free selective intermolecular C(sp3)-H amination catalyzed by an iminium salt

This report details the first organocatalytic method for nitrenoid transfer and its application to intermolecular, site-selective C(sp3)-H amination. The method utilizes a trifluoromethyl iminium salt as the catalyst, iminoiodinanes as the nitrogen source, and substrate as the limiting reagent. Activated, benzylic, and aliphatic substrates can all be selectively functionalized in yields up to 87%. A mechanistic proposal for the observed reactivity supported by experimental evidence invokes the intermediacy of a diaziridinium salt or related organic nitrenoid, species that have not been previously explored for the purpose of C-H amination. Finally, examples of late-stage functionalization of complex molecules highlight the selectivity and potential utility of this catalytic method in synthesis.

Yttrium-Catalyzed Intramolecular Hydroalkoxylation/Claisen Rearrangement Sequence: Efficient Synthesis of Medium-Sized Lactams

An efficient yttrium-catalyzed intramolecular hydroalkoxylation/Claisen rearrangement sequence has been achieved, thus enabling facile access to a diverse array of valuable medium-sized lactams. Furthermore, a mechanistic rationale for this novel cascade

Efficient photolytic C-H bond functionalization of alkylbenzene with hypervalent iodine(iii) reagent

A practical approach to radical C-H bond functionalization by the photolysis of a hypervalent iodine(iii) reagent is presented. The photolysis of [bis(trifluoroacetoxy)iodo]benzene (PIFA) leads to the generation of trifluoroacetoxy radicals, which allows the smooth transformation of various alkylbenzenes to the corresponding benzyl ester compounds under mild reaction conditions.

Metal-Free Amidation of Ethers with N, N -Dibromosulfonamides

A new metal-free amidation of ethers with N,N-dibromosulfonamides has been developed. A series of hemiaminal ethers or imines were prepared with moderate to good yields.

Efficient C(sp3)-H bond functionalization of isochroman by azadol catalysis

A novel organocatalytic C(sp3)-H bond functionalization of isochroman under practical conditions has been developed. In the presence of 5.0 mol % of AZADOL, the catalysis proceeded successfully with a broad range of substrates and nucleophiles in excellent yields.

Organocatalytic approach for C(sp3)-H bond arylation, alkylation, and amidation of isochromans under facile conditions

A new catalytic approach for the synthesis of isochroman derivatives via direct C(sp3)-H bond arylation is described. The oxidation reaction with [bis(trifluoroacetoxy)iodo]benzene facilitates the regeneration of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in the C(sp3)-H bond arylation of isochroman. The reaction conditions can also be used for alkyl Grignard reagents and amides to afford the corresponding isochroman derivatives.

Syntheses of a novel fluorinated trisphosphinoborate ligand and its copper and silver complexes. Catalytic activity toward nitrene transfer reactions

A novel fluorinated ligand, the anionic PhB(CH2P(p-CF 3C6H4)2)3 (PhBP 3 p-CF3Ph), has been synthesized and characterized, as well as its corresponding thallium, copper

Nonheme iron-mediated amination of C(sp3)-H bonds. Quinquepyridine-supported iron-imide/nitrene intermediates by experimental studies and DFT calculations

The 7-coordinate complex [Fe(qpy)(MeCN)2](ClO4) 2 (1, qpy = 2,2′:6′,2″:6″, 2′′′:6′′′,2′′′′- quinquepyridine) is a highly active nonheme iron catalyst for intra- and intermolecular amination of C(sp3)-H bonds. This complex effectively catalyzes the amination of limiting amounts of not only benzylic and allylic C(sp3)-H bonds of hydrocarbons but also the C(sp3)-H bonds of cyclic alkanes and cycloalkane/linear alkane moieties in sulfamate esters, such as those derived from menthane and steroids cholane and androstane, using PhI=NR or "PhI(OAc)2 + H2NR" [R = Ts (p-toluenesulfonyl), Ns (p-nitrobenzenesulfonyl)] as nitrogen source, with the amination products isolated in up to 93% yield. Iron imide/nitrene intermediates [Fe(qpy)(NR)(X)]n+ (CX, X = NR, solvent, or anion) are proposed in these amination reactions on the basis of experimental studies including ESI-MS analysis, crossover experiments, Hammett plots, and correlation with C-H bond dissociation energies and with support by DFT calculations. Species consistent with the formulations of [Fe(qpy)(NTs)2] 2+ (CNTs) and [Fe(qpy)(NTs)]2+ (C) were detected by high-resolution ESI-MS analysis of the reaction mixture of 1 with PhI=NTs (4 equiv). DFT calculations revealed that the reaction barriers for H-atom abstraction of cyclohexane by the ground state of 7-coordinate C NTs and ground state of C are 15.3 and 14.2 kcal/mol, respectively, in line with the observed high activity of 1 in catalyzing the C-H amination of alkanes under mild conditions.

Transition-metal-free benzylic C-H bond intermolecular amination utilizing chloramine-T and I2

An intermolecular benzylic C-H bond amination utilizing the combination of chloramine-T and I2 without the aid of transition-metal catalysts has been developed. The reaction was found applicable to a variety of benzene-substituted alkanes, as w