13745-35-2Relevant academic research and scientific papers
Catalytic C?H/C?F Coupling of Azoles and Acyl Fluorides
Ogiwara, Yohei,Iino, Yurika,Sakai, Norio
, p. 6513 - 6516 (2019)
A method for the palladium/copper-catalyzed direct acylation of azoles with acyl fluorides is described. This study reports the first examples of acyl fluorides being used as acylation reagents in transition-metal-catalyzed aromatic C?H bond functionalization reactions. Depending on the reaction temperature, decarbonylative coupling may also occur. Mechanistic studies suggest that the cleavage of the aromatic C?H bond, promoted by a copper-phosphine species, is not the rate-limiting step of this acylation.
Co/NHPI-mediated aerobic oxygenation of benzylic C-H bonds in pharmaceutically relevant molecules
Hruszkewycz, Damian P.,Miles, Kelsey C.,Thiel,Stahl, Shannon S.
, p. 1282 - 1287 (2017/02/10)
A simple cobalt(ii)/N-hydroxyphthalimide catalyst system has been identified for selective conversion of benzylic methylene groups in pharmaceutically relevant (hetero)arenes to the corresponding (hetero)aryl ketones. The radical reaction pathway tolerates electronically diverse benzylic C-H bonds, contrasting recent oxygenation reactions that are initiated by deprotonation of a benzylic C-H bond. The reactions proceed under practical reaction conditions (1 M substrate in BuOAc or EtOAc solvent, 12 h, 90-100 °C), and they tolerate common heterocycles, such as pyridines and imidazoles. A cobalt-free, electrochemical, NHPI-catalyzed oxygenation method overcomes challenges encountered with chelating substrates that inhibit the chemical reaction. The utility of the aerobic oxidation method is showcased in the multigram synthesis of a key intermediate towards a drug candidate (AMG 579) under process-relevant reaction conditions.
Palladium(II)/N-heterocyclic carbene-catalyzed direct C-H acylation of heteroarenes with N-acylsaccharins
Karthik, Shanmugam,Gandhi, Thirumanavelan
, p. 5486 - 5489 (2017/11/06)
N-Acylsaccharin represents a facile acyl group transfer agent to heteroarenes in the presence of Pd(II)/NHC complexes appended with a pyrene unit. Catalytic acylation of heteroarenes was enhanced by the noncovalent interaction between the pyrene unit and
Phosphite-oxazole/imidazole ligands in asymmetric intermolecular Heck reaction
Mazuela, Javier,Tolstoy, Paivi,Pamies, Oscar,Andersson, Pher G.,Dieguez, Montserrat
scheme or table, p. 941 - 946 (2011/03/22)
We describe the application of a new class of ligands -the phosphite-oxazole/imidazole (L1-L5a-g) - in asymmetric intermolecular Pd-catalyzed Heck reactions under thermal and microwave conditions. These ligands combine the advantages of the oxazole/imidaz
HETEROARYLATION OF ORGANOMETALLIC DERIVATIVES OF AZOLES BY N-ACYLBENZOPYRIDINIUM SALTS
Sheinkman, A. K.,Chmilenko, T. S.,Nezdiiminoga, T. N.,Tertov, B. A.,Koshchienko, Yu. V.,Klyuev, N. A.
, p. 384 - 387 (2007/10/02)
The dimerization products 1,1'-dimethyl-2,2'-bibenzimidazolyl and 2,2'-dibenzoyl-1,1',2,2'-tetrahydro-1,1'-biisoquinoline were isolated in the reaction of 1-methyl-2-imidazolyl- and 1-methyl-2-benzimidazolylmagnesium bromides with isoquinoline (quinoline) in the presence of benzoyl chloride together with the products from the heteroarylation of benzimidazole (imidazole).Their formation indicates the possibility of reaction by the SET mechanism.
Nucleophilic Acylation of Benzimidazole
Khristich, B. I.,Simonov, A. M.,Shepelenko, E. N.,Yatsimirskii, V. A.
, p. 87 - 90 (2007/10/02)
Conditions that make it possible to realize the direct C(2) acylation of benzimidazole and some of its derivatives were found.It is shown that bis products, which are converted to 2-acylbenzimidazoles upon heating to 140-200 deg C with acyl halides in the
Chromic Acid Oxidation of Some Benzimidazole Derivatives
Chattopadhyay, Subhagata
, p. 242 - 243 (2007/10/02)
Chromic acid oxidation of some benzimidazole derivatives has been carried out.The results indicate that unlike 1,2-disubstituted-4-quinazolinones , in 1,2-disubstituted benzimidazoles the hetero ring double bond does not unde
