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Relevant academic research and scientific papers

Metal-Free Electrophilic Phosphination/Cyclization of Alkynes

A metal-free electrophilic phosphination reaction has been developed. Electrophilic phosphorus species generated in situ from secondary phosphine oxides and Tf2O smoothly couple with alkynes possessing pendant nucleophiles to afford the corresponding phosphinated cyclization products in good yield. Preliminary NMR studies show that phosphirenium species may be involved as intermediates of the cyclization reactions.

Design, Synthesis, and Application of Highly Reducing Organic Visible-Light Photocatalysts

A series of inexpensive, easily tunable, and highly reducing organic photocatalysts (PCs) that exhibit strong absorption in the visible region are described. Time-dependent density functional theory calculations were applied to corroborate the experimental observations and explain the relationship between the structure and property. The photocatalytic efficiency of these PCs was demonstrated by catalyzing several challenging reactions and the radical cascade cyclization of 1,6-diyne with superior photocatalytic efficiency to other organic photocatalysts.

Copper-Catalyzed Cycloaddition between Secondary Phosphine Oxides and Alkynes: Synthesis of Benzophosphole Oxides

Benzophosphole derivatives have attracted significant attention as promising organic optoelectronic materials. We have successfully developed a copper (2mol%)/tert-butyl hydroperoxide (2equiv.) catalyst system for reaction of readily available secondary phosphine oxides and alkynes in acetonitrile at 60 C under air, which provides a rapid access to a structurally diverse array of benzophosphole oxides in moderate to good yields within 30min. The method can be easily used for a large-scale preparation. Preliminary mechanistic studies revealed that the addition of a phosphoryl radical onto a triple bond followed by cyclization on the phenyl moiety of the secondary phosphine oxide might occur to form the benzophosphole oxide.

Regioselective radical arylation: Silver-mediated synthesis of 3-phosphorylated coumarins, quinolin-2(1: H)-one and benzophosphole oxides

A silver-mediated domino radical addition/cyclization reaction of diarylphosphine oxides with propynoic acid derivatives is described in this article. The reaction of diarylphosphine oxides with alkynoates or propynoic amide was regioselective, producing 3-phosphorylated coumarins and benzophosphole oxides in moderate to good isolated yield, respectively. The hydrogen bond between PO and N-H was proposed to assist the vinyl radical regioselective arylation process. The reaction conditions were also compatible with the conversion of dialkylphosphine oxides to 3-phosphorylated-coumarins and quinolin-2(1H)-one in good yields.

Metal-Free, Visible-Light-Promoted Synthesis of 3-Phosphorylated Coumarins via Radical C?P/C?C Bond Formation

A metal-free, visible-light-promoted direct difunctionalization of alkynoates was achieved under mild conditions. By employing catalytic quantities of the commercially available Eosin Y (EY) as the photocatalyst and tert-butyl-hydroperoxide (TBHP) as the oxidant, we developed a radical tandem phosphorylation/cyclization reaction to synthesize various 3-phosphorylated coumarins with high functional group tolerance, moderate to good yields, and excellent regioselectivities. (Figure presented.).

Silver-catalyzed synthesis of 3-phosphorated coumarins via radical cyclization of alkynoates and dialkyl H -phosphonates

Ag2CO3-catalyzed difunctionalization of alkynes via a radical phosphonation and C-H functionalization tandem process was developed to synthesize various 3-phosphonated coumarins in moderate to high yields with high regioselectivity. A catalytic amount of cheap and nontoxic silver salt was employed in the domino C-P and C-C formation of alkynoates for the first time. Mechanistic studies indicate that the reaction pathway might proceed via the generation and cyclization of a phosphonated vinyl radical intermediate.