110684-40-7Relevant academic research and scientific papers
Cascade Reductive Friedel-Crafts Alkylation Catalyzed by Robust Iridium(III) Hydride Complexes Containing a Protic Triazolylidene Ligand
Albrecht, Martin,Alshakova, Iryna D.
, p. 8999 - 9007 (2021/07/31)
The synthesis of complex molecules like active pharmaceutical ingredients typically requires multiple single-step reactions, in series or in a modular fashion, with laborious purification and potentially unstable intermediates. Cascade processes offer attractive synthetic remediation as they reduce time, energy, and waste associated with multistep syntheses. For example, triarylmethanes are traditionally prepared via several synthetic steps, and only a handful of cascade routes are known with limitations due to high catalyst loadings. Here, we present an expedient catalytic cascade process to produce triarylmethanes. For this purpose, we have developed a bifunctional iridium system as the efficient catalyst to build heterotriaryl synthons via reductive Friedel-Crafts alkylation from ketones, arenes, and hydrogen. The catalytically active species were generated in situ from a robust triazolyl iridium(III) hydride complex and acid and is composed of a metal-bound hydride and a proximal ligand-bound proton for reversible dihydrogen release. These complexes catalyze the direct hydrogenation of ketones at slow rates followed by dehydration. Appropriate adjustment of the conditions successfully intercepts this dehydration and leads instead to efficient C-C coupling and Friedel-Crafts alkylation. The scope of this cascade process includes a variety of carbonyl substrates such as aldehydes, (alkyl)(aryl)ketones, and diaryl ketones as precursor electrophiles with arenes and heteroarenes for Friedel-Crafts coupling. The reported method has been validated in a swift one-step synthesis of the core structure of a potent antibacterial agent. Excellent yields and exquisite selectivities were achieved for this cascade process with unprecedentedly low iridium loadings (0.02 mol %). Moreover, the catalytic activity of the protic system is significantly higher than that of an N-methylated analogue, confirming the benefit of the Ir-H/N-H hydride-proton system for high catalytic performance.
Triazolines. 19. Nickel Peroxide Oxidation of Δ2-1,2,3-Triazolines. A Versatile General Synthetic Route to 1H-1,2,3-Triazoles
Kadaba, Pankaja K.,Edelstein, Steven B.
, p. 5891 - 5894 (2007/10/02)
Although the oxidative dehydrogenation of Δ2-1,2,3-triazolines using potassium permanganate in a phase-transfer catalyzed reaction system affords a convenient route for the synthesis of a number of 1-aryl-5-heteroaryl-substituted 1H-1,2,3-triaz
Triazolines. 14. 1,2,3-Triazolines and Triazoles, a New Class of Anticonvulsants. Drug Design and Structure-Activity Relationships
Kadaba, Pankaja
, p. 196 - 203 (2007/10/02)
Pioneering studies in our laboratory have led to the emergence og the Δ2-1,2,3-triazolines (4,5-dihydro-1H-1,2,3-triazoles) and the closely related 1H-1,2,3-triazoles as a unique family of anticonvulsant agents hitherto unknown.Unlike the tradi
