942-92-7Relevant articles and documents
Chemical synthesis of mesoporous carbon nitrides using hard templates and their use as a metal-free catalyst for Friedel-Crafts reaction of benzene
Goettmann, Frederic,Fischer, Anna,Antonietti, Markus,Thomas, Arne
, p. 4467 - 4471 (2006)
(Figure Presented) In the footsteps of Liebig and Berzelius: A material first synthesized in 1834, carbon nitride (C3N4), was synthesized in a graphitic mesoporous form by using silica nanoparticles as templates. The resulting electron-rich solid is an active catalyst for the Friedel-Crafts acylation of benzene with hexanoyl chloride. Presumably the catalysis arises from a shift of electron density from the MOs of the catalyst to the unoccupied orbitals of benzene (see picture).
Direct conversion of secondary propargyl alcohols into 1,3-di-arylpropanoneviaDBU promoted redox isomerization and palladium assisted chemoselective hydrogenation in a single pot operation
Bera, Mrinal K.,Chandra, Shubhadeep,De, Rimpa,Savarimuthu, S. Antony
, p. 17871 - 17877 (2021/10/12)
Palladium(ii)acetate is found to be an efficient catalyst for the single-step conversion of secondary propargyl alcohols to 1,3-diarylpropanone derivatives under mild basic conditions. The reaction is believed to proceedviaredox isomerisation of secondary propargyl alcohols followed by chemoselective reduction of an enone double bond with formic acid as an adequate hydrogen donor. A large number of 1,3-diarylpropanone derivatives may readily be prepared from a milligram to a multigram scale.
Combined Theoretical and Experimental Studies Unravel Multiple Pathways to Convergent Asymmetric Hydrogenation of Enamides
Yang, Jianping,Massaro, Luca,Krajangsri, Suppachai,Singh, Thishana,Su, Hao,Silvi, Emanuele,Ponra, Sudipta,Eriksson, Lars,Ahlquist, M?rten S. G.,Andersson, Pher G.
supporting information, p. 21594 - 21603 (2021/12/27)
We present a highly efficient convergent asymmetric hydrogenation of E/Z mixtures of enamides catalyzed by N,P-iridium complexes supported by mechanistic studies. It was found that reduction of the olefinic isomers (E and Z geometries) produces chiral amides with the same absolute configuration (enantioconvergent hydrogenation). This allowed the hydrogenation of a wide range of E/Z mixtures of trisubstituted enamides with excellent enantioselectivity (up to 99% ee). A detailed mechanistic study using deuterium labeling and kinetic experiments revealed two different pathways for the observed enantioconvergence. For α-aryl enamides, fast isomerization of the double bond takes place, and the overall process results in kinetic resolution of the two isomers. For α-alkyl enamides, no double bond isomerization is detected, and competition experiments suggested that substrate chelation is responsible for the enantioconvergent stereochemical outcome. DFT calculations were performed to predict the correct absolute configuration of the products and strengthen the proposed mechanism of the iridium-catalyzed isomerization pathway.
