1126682-65-2

Upstream product

• 104-51-8 1-butylbenzene 
• 70-55-3 toluene-4-sulfonamide 
• 7080-50-4 chloramine-T hydrate 
• 127-65-1 chloroamine-T 
• 21849-40-1 dibromamine-T 
• 332902-04-2 N-butylidene-4-methylbenzenesulfonamide 
• 98-80-6 phenylboronic acid 

Downstream Products

• 24517-59-7 2-phenyl-1-(4-methylbenzenesulfonyl)pyrrolidine 

Relevant academic research and scientific papers

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

Site-Selective Electrochemical Benzylic C?H Amination

C?H/N-H cross-coupling is an ideal strategy to synthesize various amines but remains challenging owing to the requirement for sacrificial chemical oxidants and the difficulty in controlling the regio- and chemo-selectivity. Herein we report a site-selective electrochemical amination reaction that can convert benzylic C?H bonds into C-N linkages via H2 evolution without need for external oxidants or metal catalysts. The synthetic strategy involves anodic cleavage of benzylic C?H to form a carbocation intermediate, which is then trapped with an amine nucleophile leading to C?N bond formation. Key to the success is to include HFIP as a co-solvent to modulate the oxidation potentials of the alkylbenzene substrate and the aminated product to avoid overoxidation of the latter.

Halogen-Bond-Induced Consecutive Csp3-H Aminations via Hydrogen Atom Transfer Relay Strategy

The utilization of a halogen bond in a number of chemical fields is well-known. Surprisingly, the incorporation of this useful noncovalent interaction in chemical reaction engineering is rare. We disclose here an uncommon use of halogen bonding to induce intermolecular Csp3-H amination while enabling a hydrogen atom transfer relay strategy to access privileged pyrrolidine structures directly from alkanes. Mechanistic studies support the presence of multiple halogen bond interactions at distinct reaction stages.

Chiral diphosphane- and NHC-containing ruthenium catalysts for the catalytic asymmetric arylation of aldimines with organoboron reagents

For the first time, we report the application of [RuCl2(η 6-p-cymene)]2 in the arylation of N-activated aldimines with boronic acids and its derivatives to afford chiral amines, which are important intermediates in the syntheses of key bioactive compounds. The behavior of the chiral ligands, the imine substrates, and the organoboron reagents were studied. Very good enantioselectivities were obtained. A new method is presented for the synthesis of chiral substituted amines by employing Ru catalysts along with known chiral phosphane ligands and a new NHC-type chiral ligand. Organoboron reagents were applied as the aryl transfer agents. High enantioselectivities were achieved with this new method, and some mechanistic insights are provided.

A highly efficient catalyst-free protocol for C-H bond activation: Sulfamidation of alkyl aromatics and aldehydes

A catalyst-free protocol has been developed for amidation of alkyl aromatics and aldehydes using TsNBr2via a nitrene transfer process in the presence of a base in excellent yield within a short time. The reaction was found to be selective for secondary and tertiary benzylic C-H bonds and C-H bonds of aldehydic groups.

Sulfonylamidation of alkylbenzenes at benzylic position with p-toluenesulfonamide and 1,3-diiodo-5,5-dimethylhydantoin

Treatment of alkylbenzenes with p-toluenesulfonamide and 1,3-diiodo-5,5-dimethylhydantoin (DIH) in a small amount of carbon tetrachloride at 60 °C gave the corresponding α-p-toluenesulfonylamido)alkylbenzenes in good to moderate yields. The present reaction is a simple method for the α-sulfonylamidation of the benzylic position in alkylbenzenes.

Catalytic enantioselective arylation of N-tosylarylimines with arylboronic acids using C2-symmetric cationic N-heterocyclic carbene Pd 2+ diaquo complexes

The asymmetric arylation of N-tosylimines with arylboronic acids was realized by using chiral cationic C2-symmetric N-heterocyclic carbene (NHC) Pd2+ diaquo complex 5b as the catalyst in combination with 1.0 equiv of K3PO

Transition-metal-free intermolecular amination of sp3 C-H bonds with sulfonamides

An efficient transition-metal-free intermolecular benzylic amidation with sulfonamides is described. Various valuable nitrogen-containing compounds, including amines, β-chloro amine, amino alcohol, α-, β-amino ester, and N-sulfonyl imine, are generated fr