61582-48-7Relevant academic research and scientific papers
Photocatalytic (Het)arylation of C(sp3)-H Bonds with Carbon Nitride
Das, Saikat,Murugesan, Kathiravan,Villegas Rodríguez, Gonzalo J.,Kaur, Jaspreet,Barham, Joshua P.,Savateev, Aleksandr,Antonietti, Markus,K?nig, Burkhard
, p. 1593 - 1603 (2021/02/09)
Graphitic carbon nitride materials have attracted significant interest in recent years and found applications in diverse light-to-energy conversions such as artificial photosynthesis, CO2 reduction, or degradation of organic pollutants. However, their utilization in synthetic photocatalysis, especially in the direct functionalization of C(sp3)-H bonds, remains underexplored. Herein, we report mesoporous graphitic carbon nitride (mpg-CN) as a heterogeneous organic semiconductor photocatalyst for direct arylation of C(sp3)-H bonds in combination with nickel catalysis. Our protocol has a broad synthetic scope (>70 examples including late-stage functionalization of drugs and agrochemicals), is operationally simple, and shows high chemo- and regioselectivities. Facile separation and recycling of the mpg-CN catalyst in combination with its low preparation cost, innate photochemical stability, and low toxicity are beneficial features overcoming typical shortcomings of homogeneous photocatalysis. Detailed mechanistic investigations and kinetic studies indicate that an unprecedented energy-transfer process (EnT) from the organic semiconductor to the nickel complex is operating.
Rh-catalyzed borylation of N-adjacent C(sp3)-H bonds with a silica-supported triarylphosphine ligand
Kawamorita, Soichiro,Miyazaki, Tatsuya,Iwai, Tomohiro,Ohmiya, Hirohisa,Sawamura, Masaya
supporting information; experimental part, p. 12924 - 12927 (2012/10/08)
Direct C(sp3)-H borylation of amides, ureas, and 2-aminopyridine derivatives at the position α to the N atom, which gives the corresponding α-aminoalkylboronates, has been achieved with a heterogeneous catalyst system consisting of [Rh(OMe)(cod)]2 and a silica-supported triarylphosphine ligand (Silica-TRIP) that features an immobilized triptycene-type cage structure with a bridgehead P atom. The reaction occurs not only at terminal C-H bonds but also at internal secondary C-H bonds under mild reaction conditions (25-100 °C, 0.1-0.5 mol % Rh).
N-Alkylamidomethylation at Electron-rich Carbons in the 1,3,5-Trialkylhexahydro-1,3,5-triazine-Acetyl Chloride System
Ikeda, Kiyoshi,Morimoto, Toshiaki,Sekiya, Minoru
, p. 1178 - 1182 (2007/10/02)
A new N-alkylamidomethylation reaction at electron-rich carbons has been developed using 1,3,5-trialkylhexahydro-1,3,5-triazine in the presence of acetyl chloride.This reaction was carried out not only with aromatics such as phenols, alkoxybenzenes and aromatic amines, but also olefins such as styrene and vinyl ethers. Keywords---N-alkylamidomethylation; electrophilic substitution; 1,3,5-trialkylhexahydro-1,3,5-triazines; acetyl chloride; aromatics; styrene; vinyl ethers
