873692-64-9

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 2645-02-5 methyl tosylglycinate 
• 106-95-6 allyl bromide 
• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 96-32-2 bromoacetic acid methyl ester 

Downstream Products

• 873692-57-0 N-allyl-N-(toluene-4-sulfonyl)-2-aminoacetaldehyde O-tert-butyldimethylsilyloxime 
• 873692-52-5 N-allyl-N-(toluene-4-sulfonyl)-2-aminoacetaldehyde oxime 
• 871123-29-4 4-[allyl-(toluene-4-sulfonyl)-amino]-N,N-dimethyl-3-oxo-butyramide 
• 361459-74-7 4-methyl-N-(2-oxoethyl)-N-2-propen-1-ylbenzenesulfonamide 

Relevant academic research and scientific papers

Olefin Oxyamination with Unfunctionalized N-Alkylanilines

N-Alkylanilines have rarely been used in oxyamination reactions, due to the normally necessary pre-functionalization of the N-atom. Also, the formation of aminium radical cations (ARCs) of anilines bearing alkyl substituents is plagued by the ARC's tendency to instantaneously convert to α-amino radicals or iminium ions. We present a readily available reagent combination that addresses both challenges, and thus allows for an oxyamination with N-alkylanilines via ARCs as the crucial reactive intermediates and excellent diastereoselectivity. (Figure presented.).

Nitroxyl Catalysts for Six-Membered Ring Bromolactonization and Intermolecular Bromoesterification of Alkenes with Carboxylic Acids

We developed a nitroxyl-catalyzed bromoesterification of alkenes with bromo reagents, which includes a six-membered ring bromolactonization of alkenyl carboxylic acids catalyzed by AZADO as the nitroxyl radical catalyst, and an intermolecular bromoesterification of alkenes with carboxylic acids using NMO as the N-oxide catalyst. We also accomplished a remote diastereoselective bromohydroxylation via an AZADO-catalyzed six-membered ring bromolactonization and a subsequent ring cleavage reaction with alkylamines to furnish ?-bromo-δ-hydroxy amides with high diastereoselectivity.

Thiyl radical-mediated cyclization of ω-alkynyl O-tert-butyldiphenylsilyloximes

ω-Alkynyl O-tert-butyldiphenylsilyloximes, upon treatment with odorless 4-tert-butylbenzenethiol in the presence of azobisisobutyronitrile (AIBN) in refluxing benzene, underwent addition of a thiyl radical to the alkynyl group followed by radical cyclizat

Catalytic olefin hydroamination with aminium radical cations: A photoredox method for direct C-N bond formation

While olefin amination with aminium radical cations is a classical method for C-N bond formation, catalytic variants that utilize simple 2° amine precursors remain largely undeveloped. Herein we report a new visible-light photoredox protocol for the intramolecular anti-Markovnikov hydroamination of aryl olefins that proceeds through catalytically generated aminium radical intermediates. Mechanistic studies are consistent with a process involving amine oxidation via electron transfer, turnover-limiting C-N bond formation, and a second electron transfer step to reduce a carbon-centered radical, rendering the overall process redox-neutral. A range of structurally diverse N-aryl heterocycles can be prepared in good to excellent yields under conditions significantly milder than those required by conventional aminium-based protocols.

Aerobic oxidative cyclization under Pd(II) catalysis: A regioselective approach to heterocycles

(Chemical Equation Presented) An efficient Yb(OTf)3-promoted palladium-catalyzed oxidative cyclization of γ-heteroalkenyl β-keto amides has been developed. Under simple aerobic condition, a variety of six-, seven-, and eight-membered-ring N- an

Intramolecular cycloaddition of O-tert-butyldimethylsilyloximes in the presence of BF3-OEt2

Intramolecular cycloaddition of novel 1,3-dipoles, N-boranonitrones, was examined. Treatment of O-tert-butyldimethylsilyloximes 9-12 having olefin moieties with 2 equiv of BF3·OEt2 generated N-boranonitrones, which underwent intramolecular cycloaddition to afford N-nonsubstituted cycloadducts 16 (and/or 18) after extractive workup. Despite the Lewis-acidic conditions, the olefin geometry of the substrates was retained in the cycloadducts in the present cycloaddition. The electronic nature of the N-boranonitrones appeared to be electrophilic. In the case of substrate 11c, having an electron-donating methyl group at an internal position of the olefin moiety, the cycloaddition gave the bridged cycloadduct 18b. The cycloaddition proceeded at relatively low temperature, and the diastereoselectivity was high.