16573-53-8

Upstream product

• 6498-34-6 cyclohexylhydrazine 
• 3128-77-6 2-isocyanobiphenyl 
• 98-89-5 Cyclohexanecarboxylic acid 
• 108-85-0 1-bromocyclohexane 
• 229-87-8 phenanthridine 
• 48153-94-2 N-methoxyphenanthridin-5-ium 
• 110-83-8 cyclohexene 
• 446065-11-8 cyclohexyltrifluoro-λ⁴-borane potassium salt 
• 108-93-0 cyclohexanol 
• 35448-12-5 2-(cyclohexyloxy)-2-oxoacetic acid 
• 4441-56-9 cyclohexylboronic acid 
• 14548-01-7 phenanthridine N-oxide 
• 110-82-7 cyclohexane 
• 125764-09-2 tetraethylammonium bis<α,α-bis(trifluoromethyl)benzenemethanolato(2-)-C²,O>cyclohexylsilicate 

Downstream Products

• 2720-93-6 6-phenylphenanthridine 

Relevant academic research and scientific papers

Transition Metal-Free Oxidative Radical Decarboxylation/Cyclization for the Construction of 6-Alkyl/Aryl Phenanthridines

A radical cascade decarboxylation/cyclization of 2-isocyanobiphenyls with aliphatic carboxylic acids as well as aromatic carboxylic acids under the transition metal-free conditions was reported. This process, which included formation of two new C-C bonds and cleavage of C-COOH bonds, afforded a novel and environmentally friendly approach to producing 6-alkyl/aryl phenanthridines with moderate to good yields.

Silver(I)-mediated reaction of 2-isocyanobiaryl with alkyl trifluoroborates: Efficient synthesis of 6-Alkylated phenanthridines

A silver-mediated free-radical cascade cyclization of isocyanides with potassium alkyl trifluoroborates was developed. The procedure tolerates a series of functional groups, including chloro, bromo, ester, ketone, and amide. Additionally, it is not sensitive to steric hindrance. Thus, this reaction represents a very useful strategy for the production of 6-Alkylated phenanthridine derivatives. The addition of alkyl radical to the isonitrile, followed by a radical aromatic cyclization, is involved in this transformation.

A Metal–Organic Framework as a Multiphoton Excitation Regulator for the Activation of Inert C(sp3)?H Bonds and Oxygen

The activation and oxidization of inert C(sp3)?H bonds into value-added chemicals affords attractively economic and ecological benefits as well as central challenge in modern chemistry. Inspired by the natural enzymatic transformation, herein,

Radical chain monoalkylation of pyridines

The monoalkylation of N-methoxypyridinium salts with alkyl radicals generated from alkenes (via hydroboration with catecholborane), alkyl iodides (via iodine atom transfer) and xanthates is reported. The reaction proceeds under neutral conditions since no acid is needed to activate the heterocycle and no external oxidant is required. A rate constant for the addition of a primary radical to N-methoxylepidinium >107 M-1 s-1 was experimentally determined. This rate constant is more than one order of magnitude larger than the one measured for the addition of primary alkyl radicals to protonated lepidine demonstrating the remarkable reactivity of methoxypyridinium salts towards radicals. The reaction has been used for the preparation of unique pyridinylated terpenoids and was extended to a three-component carbopyridinylation of electron-rich alkenes including enol esters, enol ethers and enamides.

Development of a Quinolinium/Cobaloxime Dual Photocatalytic System for Oxidative C-C Cross-Couplings via H2Release

Designing molecular photocatalysts for potent photochemical reactivities ranks among the most challenging but rewarding endeavors in synthetic photochemistry. Herein, we document a quinoline-based organophotoredox catalyst, 2,4-bis(4-methoxyphenyl)quinoli

Preparation of 6-substituted phenanthridines from o-biaryl ketoximes via the Beckmann rearrangement

Treatment of anti alkyl o-biaryl ketoximes and anti aryl o-biaryl ketoximes with Tf2O at 120 °C, followed by quenching with Et3N gave 6-alkylphenanthridines and 6-arylphenanthridines in good yields, respectively. These reactions proceeded through the O-triflation of the ketoximes, the Beckmann rearrangement, and the electrophilic cyclization of the formed nitrilium group onto the aromatic ring.

C-H alkylation of heteroarenes with alkyl oxalates by molecular photoelectrocatalysis

An oxidant- and metal-free photoelectrocatalytic C-H alkylation reaction of heteroarenes with alkyl oxalates has been developed. Several classes of heteroaromatics, such as quinolines, isoquinolines, pyridines, and phenanthridines, can be alkylated with t

Electro-oxidative C-H alkylation of quinoxalin-2(1: H)-ones with organoboron compounds

Radical cleavage of C-B bonds to accomplish C-H functionalization is synthetically appealing but practically challenging. We report herein a mild electro-oxidative method for efficient C-H alkylation of quinoxalin-2(1H)-ones by means of radical addition reactions of alkyl boronic acids and esters and alkyl trifluoroborates to afford C-C coupled products. This journal is

An ultrastable olefin-linked covalent organic framework for photocatalytic decarboxylative alkylations under highly acidic conditions

The application of two-dimensional covalent organic frameworks (2D-COFs) as photoredox catalysts offers sustainable alternatives for visible-light-driven organic transformations. However, under highly complicated organic reaction conditions, maintaining their basic structure and photoactivity is always neglected, which impedes their potential in more organic reaction types and industrial use. Herein, we describe a visible-light-driven decarboxylative alkylation of heterocycles catalysed by an olefin-linked covalent organic framework (2D-COF-2) instead of the commonly used precious metal complexes and organic dyes. A wide range of alkylated heterocycles were selectively and efficiently synthesized under heterogeneous reaction conditions. Relying on the ultrastability of olefin linkage, 2D-COF-2 maintained its basic structure and photoactivity under highly acidic conditions. Moreover, its streamlining industrial potential was demonstrated in recycling experiments, functionalization of bioactive molecules and scale-up reactions.

Visible-light-mediated photoredox minisci C-H alkylation with alkyl boronic acids using molecular oxygen as an oxidant

Herein, we report a protocol for direct visible-light-mediated Minisci C-H alkylation reactions of heteroarenes with alkyl boronic acids using molecular oxygen as the sole oxidant. This mild protocol uses an inexpensive, green oxidant; permits efficient functionalization of various N-heteroarenes with a broad range of primary and secondary alkyl boronic acids; and is scalable to the gram level. We demonstrated the practicality and sustainability of the protocol by preparing or functionalizing several pharmaceuticals and natural products.