75505-87-2

Upstream product

• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 33966-50-6 SEC-BUTYLAMINE 
• 448-61-3 2,4,6-triphenylpyrylium tetrafluoroborate 

Downstream Products

• 580-35-8 2,4,6-triphenylpyridine 
• 85433-88-1 1-methoxy-4-(3-methylpent-1-yn-1-yl)benzene 
• 1440418-97-2 6-(sec-butyl)-2-methylquinoline 

Relevant academic research and scientific papers

Visible-Light-Induced Regioselective Deaminative Alkylation of Coumarins via Photoredox Catalysis

3-Alkylated coumarins have many applications in medicinal chemistry, however, methods access to such structures are still limited. Herein, we report a site-selective photocatalytic deaminative alkylation of coumarins utilizing pyridinium-activated aliphatic primary amines as alkylation reagents. The protocol was highlighted by its mild reaction conditions, operational simplicity, and broad functional group compatibility. Moreover, this strategy enables late-stage modification of some pharmaceuticals and natural products, thus providing an appealing approach to valuable molecules in medicinal chemistry. (Figure presented.).

The Formal Cross-Coupling of Amines and Carboxylic Acids to Form sp3–sp3 Carbon–Carbon Bonds

We have developed a deaminative–decarboxylative protocol to form new carbon(sp3)–carbon(sp3) bonds from activated amines and carboxylic acids. Amines and carboxylic acids are ubiquitous building blocks, available in broad chemical diversity and at lower cost than typical C?C coupling partners. To leverage amines and acids for C?C coupling, we developed a reductive nickel-catalyzed cross-coupling utilizing building block activation as pyridinium salts and redox-active esters, respectively. Miniaturized high-throughput experimentation studies were critical to our reaction optimization, with subtle experimental changes such as order of reagent addition, composition of a binary solvent system, and ligand identity having a significant impact on reaction performance. The developed protocol is used in the late-stage diversification of pharmaceuticals while more than one thousand systematically captured and machine-readable reaction datapoints are reposited.

Ruthenium-catalysedmeta-selective CAr-H bond alkylationviaa deaminative strategy

The use of aliphatic amines as alkylating reagents in organic synthesisviaC-N bond activation remains underdeveloped. We herein describe a novel ruthenium-catalysed and directing-group assisted protocol for the synthesis ofmeta-alkylated arenesviadual C-H and C-N activation. Bench-stable and easily handled redox-active Katritzky pyridinium salts derived from abundant amines and amino acid species were used as alkyl radical precursors. This catalytic reaction could accommodate a broad range of functional groups and provide access to variousmeta-alkylated products.

Photoredox-catalyzed synthesis of sulfones through deaminative insertion of sulfur dioxide

Katritzky salts are used as the alkyl radical precursors with the insertion of sulfur dioxide under photoredox catalysis. This transformation first enables direct generation of various alkylsulfonyl radicals by photoinduced single electron reduction, leading to diverse dialkyl sulfones in good to excellent yields. A radical pathway is proposed under visible-light induced conditions with the insertion of sulfur dioxide.

Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron Donor–Acceptor Complex

A deaminative strategy for the borylation of aliphatic primary amines is described. Alkyl radicals derived from the single-electron reduction of redox-active pyridinium salts, which can be isolated or generated in situ, were borylated in a visible light-mediated reaction with bis(catecholato)diboron. No catalyst or further additives were required. The key electron donor–acceptor complex was characterized in detail by both experimental and computational investigations. The synthetic potential of this mild protocol was demonstrated through the late-stage functionalization of natural products and drug molecules.

Deaminative Strategy for the Visible-Light-Mediated Generation of Alkyl Radicals

A deaminative strategy for the visible-light-mediated generation of alkyl radicals from redox-activated primary amine precursors is described. Abundant and inexpensive primary amine feedstocks, including amino acids, were converted in a single step into redox-active pyridinium salts and subsequently into alkyl radicals by reaction with an excited-state photocatalyst. The broad synthetic potential of this protocol was demonstrated by the alkylation of a number of heteroarenes under mild conditions.

Kinetics and Mechanism of Nucleophilic Displacements with Heterocycles as Leaving Groups. Part 10. Reactions of s-Alkyl Primary Amines with Pyryliums

2,4,6-Triphenylpyrylium with s-alkylamines gives isolatable pyridiniums (which undergo SN2 substitution with nucleophiles and elimination to olefins). 2,4,6-triphenylpyrilium with 1-phenylethylamine and α-phenylbenzylamine forms the corresponding carbonium ions which may be trapped by nucleophiles.Isolated 1-cycloalkylbenzoquinoliniums (2) solvolyse by the SN1 mechanism (for five-, six- and seven-membered rings): for the cyclobutyl case an Sn2 reaction is also found.

The Preparation of Pyridiniums from Pyryliums

Mild preparative conditions are described for the reaction of primary alkyl-, secondary alkyl-, and aryl-primary amines (including weakly basic amines) with pyryliums (including those with bulky α-substituents).Conditions were optimized by 13C n.m.r. stud