RESUMEN
We demonstrate a ligand- and glovebox-free regioselective direct C(3)-H imidation of 2-pyridones and also benzylic-type imidation of 2-pyridones bearing a methyl substituent employing Cu(OAc)2·H2O as the catalyst and N-fluorobenzenesulfonimide (NFSI) as an imidating reagent. A broad range of imidated 2-pyridone derivatives is made up to excellent yields. The present strategy operates well on a gram scale, and the ensuing product can be readily subjected to mono- and bis-desulfonylation reactions.
RESUMEN
Deuterated organic molecules have immense value in the pharmaceutical industry. Here, we present a synthetic strategy for direct trideuteromethylation of sulfenate ions derived in situ from ß-sulfinyl esters in the presence of a base utilizing inexpensive and abundant CD3OTs as the electrophilic trideuteromethylating agent. This protocol provides straightforward access to an array of trideuteromethyl sulfoxides in yields of 75-92% with a high degree of deuteration. The ensuing trideuteromethyl sulfoxide can be readily modified into trideuteromethyl sulfone and sulfoximine.
Asunto(s)
Ésteres , Sulfóxidos , Aniones , IonesRESUMEN
Imidazopyridine is an important framework that constitutes several pharmaceutical drugs and biologically active molecules. Herein, we present the palladium-catalyzed regioselective C3-allylic alkylation of 2-aryl imidazopyridines with MBH carbonates. This strategy furnishes a broad spectrum of C3-allylated imidazopyridines, and their structures have been unequivocally established using X-ray analysis. Besides, the reaction can be easily scaled up on a gram scale, and the ensuing product can be smoothly manipulated into synthetically useful entities.
RESUMEN
Biaryl and indole units are important structural motifs in several bioactive molecules and functional materials. We have accomplished straightforward access to C2-biarylated indole derivatives through palladium-catalyzed C-H activation strategy with a broad range of substrate scope in yields of 24 to 92%. Besides, the UV/visible absorption and fluorescence properties of the ensuing products were explored. The calculated higher dihedral angle and rotational barrier values for the selected C2-biarylated indoles show that these compounds may display atropisomerism at room temperature.