1378043-01-6

Upstream product

• 1015-89-0 phenanthridin-6-ol 
• 4559-70-0 Diphenylphosphine oxide 
• 19394-61-7 2-biphenylyl isothiocyanate 
• 108-86-1 bromobenzene 
• 18872-86-1 diphenylphosphine oxide 
• 3128-77-6 2-isocyanobiphenyl 
• 5346-21-4 N-formyl-2-aminobiphenyl 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

4CzIPN-tBu-Catalyzed Proton-Coupled Electron Transfer for Photosynthesis of Phosphorylated N-Heteroaromatics

2,4,5,6-Tetrakis(3,6-di-tert-butyl-9H-carbazol-9-yl)isophthalonitrile (4CzIPN-tBu) was developed as a photocatalyst for the phosphorus-radical-initiated cascade cyclization reaction of isocyanides. By using 4CzIPN-tBu as catalyst, we developed a visible-light-induced proton-coupled electron transfer strategy for the generation of phosphorus-centered radicals, via which a wide range of phosphorylated phenanthridines, quinolines, and benzothiazoles were successfully constructed.

Metal-free photo-induced radical C-P and C-S bond formation for the synthesis of 2-phosphoryl benzothiazoles

We reveal here a visible-light promoted phosphorylation of 2-isocyanoaryl thioethers for the first time with concomitant C(sp3)-S bond cleavage and imidoyl C–S formation. Additionally, this method features the use of 3 mol% organic dye Rose Bengal as the photocatalyst without external transition-metal or peroxide oxidants, and provides a novel and environmentally friendly approach for the preparation of a variety of 2-phosphoryl benzothiazoles in moderate to good yields.

Visible-light-induced tandem radical addition-cyclization of 2-aryl phenyl isocyanides catalysed by recyclable covalent organic frameworks

A visible-light-induced tandem radical addition-cyclization sequence via 2-aryl phenyl isocyanides as the starting material and two-dimensional covalent organic frameworks (2D-COFs) as the photocatalyst was developed, delivering multifarious 6-substituted phenanthridines in high yields. Benefitting from the utilization of a heterogeneous photocatalyst, this protocol features easy catalyst separation and excellent recyclability. A negligible loss of the catalytic activity was observed after multiple runs. High practicability of this protocol was further demonstrated by continuous flow experiments.

Selective P?C(sp3) Bond Cleavage and Radical Alkynylation of α-Phosphorus Alcohols by Photoredox Catalysis

Herein the first P?C(sp3) bond cleavage and radical alkynylation of α-phosphorus alcohols to construct phosphonoalkynes is reported. The phosphorus radical is generated upon P?C bond cleavage reaction via the alkoxyl radical through photoredox catalysis with cyclic iodine(III) reagents. Various arylphosphinoyl-, alkylphosphinoyl-, phosphonate-, and phosphonic amide alcohols serve as radical phosphorus precursors to construct phosphonoalkynes for the first time.

Synthesis of 6-Phosphorylated Phenanthridines by Mn(II)-Promoted Tandem Reactions of 2-Biaryl Isothiocyanates with Phosphine Oxides

A novel Mn(II)-promoted tandem phosphorylation/cyclization reaction of 2-biaryl isothiocyanates with phosphine oxides is described. This is the first general method to synthesize 6-phosporylated phenanthridines from 2-biaryl isothiocyanates. The approach is featured by oxidant-free, low loading of P-reagent, easy operation, and high functional group tolerance.

Preparation method of 6-phosphoryl substituted phenanthridine derivative

The invention discloses a preparation method of a 6-phosphoryl substituted phenanthridine derivative, and belongs to the technical field of organic synthesis. The method comprises the steps that biphenyl isothiocyanate and diaryl oxygen and phosphorus are added into a reactor, by being catalyzed by manganese, heating is conducted in a solvent, after a reaction is completed, cooling is conducted to reach room temperature, a system is diluted with ethyl acetate and washed with saturated sodium chloride, an organic phase is combined, a filtrate is concentrated through a rotary evaporator, a coarse product is obtained, and finally a product is obtained through column chromatography separation. The synthetic method is easy to implement, raw materials are easy to prepare, multiple substituent groups are introduced simultaneously, the product is easy to purify and separate, the yield is high, and the method is suitable for synthesizing the 6-phosphoryl substituted phenanthridine derivative. The reaction equation of the derivative is defined in the description.

Metal-free synthesis of 6-phosphorylated phenanthridines: Synthetic and mechanistic insights

A novel and efficient method for the generation of phosphinoyl radicals from the combination of diphenyliodonium salt (Ph2I+,-OTf) with triethylamine (Et3N) in the presence of secondary phosphine oxides is reported. By employing this practical and simple approach, a large variety of 6-phosphorylated phenanthridines have been synthesized through the addition of phosphinoyl radicals to isonitriles as radical acceptors. The reaction works smoothly in the absence of any transition metal or photocatalyst. On the basis of electron paramagnetic resonance (EPR) and density functional theory (DFT) calculations, the mechanism of this reaction is discussed.

Visible-Light-Induced Cascade Reaction of Isocyanides and N-Arylacrylamides with Diphenylphosphine Oxide via Radical C-P and C-C Bond Formation

An effective photoredox-mediated tandem phosphorylation/cyclization reaction of diphenylphosphine oxide with three types of radical acceptors leads to P(O)Ph2-containing phenanthridines, isoquinolines, and indolin-2-ones by formation of both C-

Synthesis of phenanthridin-6-yldiphenylphosphine oxides by oxidative cyclization of 2-isocyanobiphenyls with diarylphosphine oxides

A Mn(III)-promoted oxidative cyclization of 2-isocyanobiphenyls with diarylphosphine oxides is reported, providing phenanthridin-6- yldiphenylphosphine oxides in good yields. Radical phosphonation and isocyanide insertion are believed to be involved in the reaction process.

Silver-catalyzed 2-isocyanobiaryls insertion/cyclization with phosphine oxides: Synthesis of 6-phosphorylated phenanthridines

A silver-catalyzed 2-isocyanobiaryls insertion/cyclization with phosphine oxides was described for the construction of the 6-phosphorylated phenanthridines through radical addition of in situ formed P-centered radical to 2-isocyanobiphenyls and homolytic