86010-70-0Relevant articles and documents
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.
Development of a practical synthesis of an aminoindanol-derived m1 agonist
Hansen, Marvin M.,Borders, Sandra S.K.,Clayton, Marcella T.,Heath, Perry C.,Kolis, Stanley P.,Larsen, Samuel D.,Linder, Ryan J.,Reutzel-Edens, Susan M.,Smith, Justin C.,Tameze, Sheila L.,Ward, Jeffrey A.,Weigel, Leland O.
experimental part, p. 198 - 208 (2010/04/22)
An efficient and scalable synthesis of the clinical candidate 1 is described. The first-generation synthesis built the enantioenriched nitro-aminoindanol core from 6-nitroindanone using a five-step literature route. The second-generation route used a safe aromatic nitration protocol in the presence of the unprotected alcohol to afford the requisite nitro-aminoindanol in one step. Challenges addressed in the remainder of the synthesis include a nitro group reduction to afford ppm levels of unreacted Ar-NO2 (a mutagen) and a novel amidine formation under mild conditions via DMAP/K2CO3-promoted reaction with a thioimidate-activated amide. A convenient protocol for freebasing the API was provided by stirring with solid K2CO3 and monitoring disappearance of HI by reverse-phase HPLC.
