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Upstream product

• 86553-34-6 Toluene-4-sulfonic acid 2-[allyl-(toluene-4-sulfonyl)-amino]-ethyl ester 
• 98-59-9 p-toluenesulfonyl chloride 
• 70-55-3 toluene-4-sulfonamide 
• 129748-56-7 N-(2-bromoethyl)-N-(2-propenyl)-4-methylbenzenesulfonamide 
• 53226-44-1 N-(3-Methylbutyl)-4-methylbenzenesulfonamide 
• 107-85-7 1-amino-3-methylbutane 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 78-94-4 methyl vinyl ketone 
• 14316-14-4 N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide 
• 869275-29-6 N-allyl-N-(2-hydroxyethyl)-4-methylbenzenesulfonamide 
• 33611-54-0 2,2-dimethyl-1-phenylpropan-1-imine 
• 1303528-91-7 N-allyl-N-(2-chloro-ethyl)-4-methyl-benzenesulfonamide 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 109950-07-4 N-(2-methylbutyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Mechanistic studies of reactive oxygen species mediated electrochemical radical reactions of alkyl iodides

Mechanistic studies of a reactive oxygen species mediated electrochemical radical reaction of alkyl iodides are described. Hydroxyl radicals and ozone are identified to be the active species involved in the formation of alkyl radicals under mildly reducing potential (-1.0 V vs. Ag QRE) in buffered acidic conditions (pH 3.6).

Vitamin B 12-Catalyzed Dicarbofunctionalization of Bromoalkenes under Visible Light Irradiation

Vitamin B 12plays a crucial role in enzymatic transformations. This natural compound proved also useful as a catalyst in numerous organic reactions. Commercial availability and lower cost than precious metal complexes, make cobalamin an attract

Photoredox catalysis on unactivated substrates with strongly reducing iridium photosensitizers

Photoredox catalysis has emerged as a powerful strategy in synthetic organic chemistry, but substrates that are difficult to reduce either require complex reaction conditions or are not amenable at all to photoredox transformations. In this work, we show that strong bis-cyclometalated iridium photoreductants with electron-rich β-diketiminate (NacNac) ancillary ligands enable high-yielding photoredox transformations of challenging substrates with very simple reaction conditions that require only a single sacrificial reagent. Using blue or green visible-light activation we demonstrate a variety of reactions, which include hydrodehalogenation, cyclization, intramolecular radical addition, and prenylationviaradical-mediated pathways, with optimized conditions that only require the photocatalyst and a sacrificial reductant/hydrogen atom donor. Many of these reactions involve organobromide and organochloride substrates which in the past have had limited utility in photoredox catalysis. This work paves the way for the continued expansion of the substrate scope in photoredox catalysis.

Photoinduced Radical Borylation of Alkyl Bromides Catalyzed by 4-Phenylpyridine

Utilizing pyridine catalysis, we developed a visible-light-induced transition-metal-free radical borylation reaction of unactivated alkyl bromides that features a broad substrate scope and mild reaction conditions. Mechanistic studies revealed a novel nucleophilic substitution/photoinduced radical formation pathway, which could be utilized to trigger a variety of radical processes.

Cobalt-Catalyzed Tandem Radical Cyclization/C-C Coupling Initiated by Directed C-H Activation

A cobalt-N-heterocyclic carbene catalyst promotes a tandem radical cyclization/C-C coupling reaction between tosylamide-tethered bromo-alkenes and aryl N-H imines initiated by chelation-assisted arene C-H activation, affording 3-(arylmethyl)pyrrolidine de

Dehalogenative Deuteration of Unactivated Alkyl Halides Using D2O as the Deuterium Source

The general dehalogenation of alkyl halides with zinc using D2O or H2O as a deuterium or hydrogen donor has been developed. The method provides an efficient and economic protocol for deuterium-labeled derivatives with a wide substrate scope under mild reaction conditions. Mechanistic studies indicated that a radical process is involved for the formation of organozinc intermediates. The facile hydrolysis of the organozinc intermediates provides the driving force for this transformation.

A general copper-based photoredox catalyst for organic synthesis: Scope, application in natural product synthesis and mechanistic insights

Organic transformations can broadly be classified into four categories including cationic, anionic, pericyclic and radical reactions. While the last category has been known for decades to provide remarkably efficient synthetic pathways, it has long been hampered by the need for toxic reagents, which considerably limited its impact on chemical synthesis. This situation has come to an end with the introduction of new concepts for the generation of radical species, photoredox catalysis – which simply relies on the use of a catalyst that can be activated upon visible light irradiation – certainly being the most efficient one. The state-of-the-art catalysts mostly rely on the use of ruthenium and iridium complexes and organic dyes, which still considerably limits their broad implementation in chemical processes: alternative readily available catalysts based on inexpensive, environmentally benign base metals are therefore strongly needed. Furthermore, expanding the toolbox of methods based on photoredox catalysis will facilitate the discovery of new light-mediated transformations. This article details the use of a simple copper complex which, upon activation with blue light, can initiate a broad range of radical reactions.

Copper-Catalyzed Reductive Trifluoromethylation of Alkyl Iodides with Togni's Reagent

This work illustrates a reductive cross-electrophile coupling protocol for trifluoromethylation of alkyl iodides under Cu-catalyzed/Ni-promoted reaction conditions. The use of diboron esters as the terminal reductant allows the effective generation of the alkyl-CF3 products with excellent functional group tolerance and broad substrate scope. A mechanism involving a reaction of alkyl-Cu with Togni's reagent was proposed.

Palladium-catalyzed intramolecular reductive olefin hydrocarbonation: Benzylic hydrogen serving as a new hydrogen donor

A palladium-catalyzed intramolecular hydrocarbonation of unactivated alkenes was achieved, in which toluene is used as a hydrogen donor for the first time. The radical transfer hydrogenation is designed and realized based on the Bond Dissociation Energy (

A General Copper Catalyst for Photoredox Transformations of Organic Halides

A broadly applicable copper catalyst for photoredox transformations of organic halides is reported. Upon visible light irradiation in the presence of catalytic amounts of [(DPEphos)(bcp)Cu]PF6 and an amine, a range of unactivated aryl and alkyl halides were shown to be smoothly activated through a rare Cu(I)/Cu(I)?/Cu(0) catalytic cycle. This complex efficiently catalyzes a series of radical processes, including reductions, cyclizations, and direct arylation of arenes.